The Boger Group Publications
Publications
533.
T.
C. Turner, K. Shibayama, and D. L. Boger, Hypervalent
iodine(III)-promoted intermolecular C-C coupling of vindoline with
β-ketoesters and related substrates, Org.
Lett. 2013, 15, 1100–1103.
532.
J.
Xie, A. L. Wolfe, and D. L. Boger, Total synthesis of kopsinine, Org.
Lett. 2013, 15, 868–870.
531.
S.
P. Breazzano, Y. B. Poudel, and D. L. Boger, A Pd(0)-mediated indole
(macro)cyclization reaction, J. Am. Chem. Soc. 2013,
135, 1600–1606.
530.
E.
K. Leggans, K. K. Duncan, T. J. Barker, K. D. Schleicher, and D. L.
Boger, A remarkable series of vinblastine analogues displaying
enhanced activity and an unprecedented tubulin binding steric
tolerance: C20’ urea derivatives, J.
Med. Chem. 2013, 56, 628–639.
529.
K.
D. Schleicher, Y. Sasaki, A. Tam, D. Kato, K. K. Duncan, and D. L.
Boger, Total synthesis and evaluation of vinblastine analogues
containing systematic deep-seated modifications in the vindoline
subunit ring system: core redesign,
J. Med. Chem. 2013, 56, 483–495.
528.
T.
J. Barker and D. L. Boger, Fe(III)/NaBH4-mediated free
radical hydrofluorination of unactivated alkenes, J. Am. Chem. Soc. 2012,
134, 13588–13591.
527. H.
Gotoh, J. E. Sears, A. Eschenmoser, and D. L. Boger, New insights into
the mechanism and an expanded scope of the Fe(III)-mediated
vinblastine coupling reaction, J. Am. Chem. Soc. 2012,
134, 13240–13243.
526. D.
L. Boger, Inhibitors of fatty acid amide hydrolase (FAAH), in Chembiomolecular
Science:
At the Frontier of Chemistry and Biology, Shibasaki, M., Iino, M.,
Osada, H., Eds., Springer, Japan; 2012, pp 37–49.
525. A.
Okano, R. C. James, J. G. Pierce, J. Xie, and D. L. Boger,
Silver(I)-promoted conversion of thioamides to amidines: divergent
synthesis of a key series of vanomycin aglycon residue 4 amidines that
clarify binding behavior to model ligands, J. Am. Chem. Soc. 2012,
134, 8790-8793.
524.
A. L. Wolfe, K. K. Duncan, N. Parelkar, S. J. Weir, G. A. Vielhauer, and
D. L. Boger, A novel, unusually efficacious duocarmycin carbamate
prodrug that releases no residual byproduct, J. Med. Chem. 2012,
55, 5878–5886.
523. L.
R. Whitby and D. L. Boger, Comprehensive peptidomimetic libraries
targeting protein-protein interactions. Acc. Chem. Res. 2012,
45, 1698–1709.
522. J.
P. Lajiness, W. Jiang, and D. L. Boger, Divergent total synthesis of
(–)-aspidospermine and (+)-spegazzinine, Org. Lett. 2012,
14, 2078–2081.
521. L.
R. Whitby, K. E. Boyle, L. Cai, M., X. Yu, M. Gochin, and D. L. Boger,
Discovery of HIV fusion inhibitors targeting gp41 using a comprehensive
α-helix mimetic library, Bioorg. Med. Chem. Lett. 2012,
22, 2861–2865.
520.
R. C. James, J. G. Pierce, A. Okano, J. Xie, and D. L. Boger, Redesign
of glycopeptide antibiotics: back to the future, ACS Chem. Biol. 2012,
7, 797–804. (Invited Perspective)
519. E.
K. Leggans, T. J. Barker, K. K. Duncan, and D. L. Boger,
Iron(III)/NaBH4-mediated additions to unactivated alkenes: synthesis of
novel C20’ vinblastine analogues, Org. Lett. 2012,
14, 1428–1431. (Ranked best in 2012 by Organic
Letters)
518.
K. Otrubova and D. L. Boger, α-Ketoheterocycle-based inhibitors of fatty
acid amide hydrolase, ACS Chem. Neurosci. 2012,
3, 340–348. (Invited mini-review).
517. J.
Xie, A. Okano, J. G. Pierce, R. C. James, S. Stamm, C. M. Crane, and D.
L. Boger, Total synthesis of [Ψ[C(=S)NH]Tpg4]vancomycin aglycon,
[Ψ[C(=NH)NH]Tpg4]vancomycin aglycon and related key compounds:
reengineering vancomycin for dual D-Ala-D-Ala and D-Ala-D-Lac binding, J.
Am. Chem. Soc. 2012, 134, 1284–1297.
516. L. Booker, S. G. Kinsey, R. A.
Abdullah, J. L. Blankman, J. Z. Long, C. Ezzili, D. L. Boger, B. F.
Cravatt, and A. H. Lichtman, The FAAH inhibitor PF-3845 acts in the
nervous system to reverse lipopolysaccharide-induced tactile allodynia in
mice, Br. J. Pharmacol. 2012, 165,
2485–2496.
515. H. Gotoh, K. K. Duncan, W. M. Robertson, and D. L.
Boger, 10’-Fluorovinblastine and 10’-fluorovincristine: synthesis of a key
series of modified vinca alkaloids, ACS Med. Chem. Lett. 2011,
2, 948–952.
514. S. P. Breazzano and D. L. Boger, Synthesis and
stereochemical determination of complestatin A and B (neuroprotection A
and B), J. Am. Chem. Soc. 2011, 133,
18495–18502.
513. J. Xie, J. G. Pierce, R. C. James, A. Okano, and
D. L. Boger, A redesigned vancomycin engineered for dual D-Ala-D-Ala and
D-Ala-D-Lac binding exhibits potent antimicrobial activity against
vancomycin-resistant bacteria, J. Am. Chem. Soc. 2011,
133, 13946–13949.
512. E. D. Anderson and D. L. Boger, Inverse electron
demand Diels-Alder reactions of 1,2,3-triazines: pronounced subsituent
effects on reactivity and cycloaddition scope, J. Am. Chem. Soc.
2011, 133, 12285–12292.
511. K. Otrubova, C. Ezzili, and D. L. Boger,
The discovery and development of inhibitors of fatty acid amide hydrolase
(FAAH), Bioorg. Med. Chem. Lett. 2011, 21,
4674–4685. (Invited BMCL Digest)
510. L. R. Whitby, Y. Ando, V. Setola, P. K. Vogt, B.
L. Roth, and D. L. Boger, Design, synthesis and validation of a β-turn
mimetic library targeting protein–protein and peptide–receptor
interactions, J. Am. Chem. Soc. 2011, 133,
10184–10194.
509. E. D. Anderson and D. L. Boger, Scope of the
inverse electron demand Diels–Alder reactions of 1,2,3-triazine, Org.
Lett. 2011, 13, 2492–2494.
508. C. Ezzili, M. Mileni, N. McGlinckey, J. Z.
Long, S. G. Kinsey, D. G. Hochstatter, R. C. Stevens, A. H. Lichtman, B.
F. Cravatt, E. J. Bilsky, and D. L. Boger, Reversible competitive
α-ketoheterocycle inhibitors of fatty acid amide hydrolase containing
additional conformational constraints in the acyl side chain: orally
active, long acting analgesics, J. Med. Chem. 2011,
54, 2805–2822.
507. M. Mileni, J. Garfunkle, C. Ezzili, B. F. Cravatt,
R. C. Stevens, and D. L. Boger, Fluoride-mediated capture of a noncovalent
bound state of a reversible covalent enzyme inhibitor: X-ray
crystallographic analysis of an exceptionally potent α-ketoheterocycle
inhibitor of fatty acid amide hydrolase, J. Am. Chem. Soc. 2011,
133, 4092–4100.
506. C. J. Thomas, H. E. Casquilho, J. York, D. L.
DeCamp, D. Dai, E. B. Petrilli, D. L. Boger, R. A. Slayden, S. M. Amberg,
S. R. Sprang, and J. H. Nunberg, A specific interaction of small molecule
entry inhibitors with the envelope glycoprotein complex of the Junin
hemorrhagic fever arenavirus, J. Biol. Chem. 2011,
286, 6192–6200.
505. J. P. Lajiness and D. L. Boger, Asymmetric
synthesis of 1,2,9,9a-tetrahydrocyclopropa[c]benzo[e]indol-4-one (CBI),
J. Org. Chem. 2011, 76, 583–587.
504. J. P. Lajiness, W. M. Robertson, I. Dunwiddie, M.
A. Broward, G. A. Vielhauer, S. J. Weir, and D. L. Boger, Design,
synthesis, and evaluation of CC-1065 and duocarmycin O-aminophenol
prodrugs subject to tunable reductive activation, J. Med. Chem.
2010, 53, 7731–7738.
503. A. Tam, H. Gotoh, W. M. Robertson, and D. L. Boger, Catharanthine
C16 substituent effects on the biomimetic coupling with vindoline:
preparation and evaluation of a key series of vinblastine analogues, Bioorg.
Med. Chem. Lett. 2010, 20, 6408–6410.
502. J. P. Lajiness and D. L. Boger, Synthesis and characterization of a
cyclobutane duocarmycin derivative incorporating the CbB1
(1,2,10,11-tetrahydro-9H-cyclobuta[c]benzo[e]indol-4-one) alkylation
subunit,J. Am. Chem. Soc. 2010, 132, 13936-13940.
501. C. M. Crane, J. G. Pierce, S. S. F. Leung, J. Tirado-Rives, W. L.
Jorgensen, and D. L. Boger, Synthesis and evaluation of selected key
methyl ether derivatives of vancomycin aglycon, J. Med. Chem. 2010,
53, 7229-7235.
500. Y. Sasaki, D. Kato, and D. L. Boger, Asymmetric total synthesis of
vindorosine, vindoline, and key vinblastine analogues, J. Am. Chem.
Soc. 2010, 132, 13533-13544.
499. G. Ambrus, L. R. Whitby, E. L. Singer, O. Trott, E. Choi, A. J.
Olson, D. L. Boger, and L. Gerace, Small molecule peptidomimetic
inhibitors of importin ?/? mediated nuclear transport, Bioorg. Med.
Chem. 2010, 10, 7611-7620.
498. C. Ezzili, K. Otrubova, and D. L. Boger, Fatty acid amide signaling
molecules, Bioorg. Med. Chem. Lett. 2010, 20,
5959-5968.(Invited BMCL Digest).
497. P. R. Patel and D. L. Boger, Intramolecular Diels-Alder reaction of
cyclopropenone ketals, Org. Lett. 2010, 12,
3540-3543.
496. C. P. Burke, M. R. Swingle, R. E. Honkanen, and D. L. Boger, Total
synthesis and evaluation of phostriecin and key structural analogues,
J. Org. Chem. 2010, 75, 7505-7513. (Feature
Article).
495. P. R. Patel and D. L. Boger, Intramolecular [1+2] and [3+2]
cycloaddition reactions of cyclopropenone ketals, J. Am. Chem. Soc.
2010, 132, 8527-8529.
494. P. Va, E. L. Campbell, W. M. Robertson, and D. L. Boger, Total
synthesis and evaluation of a key series of C5-substituted vinblastine
derivatives, J. Am. Chem. Soc. 2010, 132,
8489-8495.
493. H. Shimamura, S. P. Breazzano, J. Garfunkle, F. S. Kimball, J. D.
Trzupek, and D. L. Boger, Total synthesis of complestatin: development of
a Pd(0)-mediated indole annulation for macrocyclization, J. Am. Chem.
Soc. 2010, 132, 7776-7783.
492. W. M. Robertson, D. B. Kastrinsky, I. Hwang, and D. L. Boger,
Synthesis and evaluation of a series of C5'-substituted duocarmycin SA
analogs, Bioorg. Med. Chem. Lett. 2010, 20,
2722--2725.
491. J. S. Oakdale and D. L. Boger, Total synthesis of lycogarubin C and
lycogalic acid, Org. Lett. 2010, 12, 1132-1134.
490. D. Kato, Y. Sasaki, and D. L. Boger, Asymmetric total synthesis of
vindoline, J. Am. Chem. Soc. 2010, 132, 3685-3687.
489. K. E. Boyle, K. S. MacMillan, D. A. Ellis, J. P. Lajiness, W. M.
Robertson, and D. L. Boger, Synthesis and evaluation of duocarmycin SA
analogs incorporating the methyl
1,2,8,8a-tetrahydrocyclopropa[c]oxazolo[2,3-e]indole-4-one-6-carboxylate
(COI) alkylation subunit,, Bioorg. Med. Chem. Lett. 2010, 20,
1854-1857.
488. E. L. Campbell, A. M. Zuhl, C. M. Liu, and D. L. Boger, Total
synthesis of (+)-fendleridine (aspidoalbidine) and
(+)-1-acetylaspidoalbidine, J. Am. Chem. Soc. 2010, 132,
3009-3012.
487. C. P. Burke, N. Haq, and D. L. Boger, Total synthesis, assignment of
relative and absolute stereochemistry, and structural reassignment of
phostriecin (aka sultriecin), J. Am. Chem. Soc. 2010, 132,
2157-2159.
486. M. J. Giffin, R. Muller, J. Savage, Y. C. Lin, S. Hong, W. Jin, L.
R. Whitby, J. H. Elder, D. L. Boger, and R. E. Torbett, Identification of
broad-based HIV-1 protease inhibitors from combinatorial libraries,
ChemBioChem. 2010, 429, 527-532.
485. J. Garfunkle, F. S. Kimball, J. D. Trzupek, S. Takazawa, H.
Shimamura, M. Tomishima, and D. L. Boger, Total synthesis of chloropeptin
II (complestatin) and chloropeptin I, J. Am. Chem. Soc. 2009,
131, 16036-1603 8.
484. K. S. MacMillan, J. P. Lajiness, C. Lopez-Cara, R. Romagnoli, W. M.
Robertson, I. Hwang, P. G. Baraldi, and D. L. Boger, Synthesis and
evaluation of a thio analogue of duocarmycin SA, Bioorg. Med. Chem.
Lett. 2009, 19, 6962-6965.
483. M. Mileni, J. Garfunkle, C. Ezzili, F. S. Kimball, B. F. Cravatt, R.
C. Stevens, and D. L. Boger, X-ray crystallographic analysis of
?-ketoheterocycle-based inhibitors bound to a humanized variant of fatty
acid amide hydrolase, J. Med. Chem. 2010, 52,
230-240.
482. J. Shi, J. S. Stover, L. R. Whitby, P. K. Vogt, and D. L. Boger,
Small molecule inhibitors of Myc/Max dimerization and Myc-induced cell
transformation, Bioorg. Med. Chem. Lett. 2009, 19,
6038-6041.
481. X. Fang, J. Nam, D. Shin, Y. Rew, D. L. Boger, and S. Walker,
Functional and biochemical analysis of a key series of ramoplanin
analogues, Bioorg. Med. Chem. Lett. 2009, 19,
6189-6191.
480. M. B. Swingle, L. Amable, B. G. Lawhorn, S. B. Buck, C. P. Burke, P.
Ratti, K. L. Fisher, D. L. Boger, and R. E. Honkanen, Structure-activity
relationship studies of fostriecin, cytostatin, and key analogs with PP1,
PP2A, PP5 and (?12 - ?13)-chimeras (PP1/PP2A and PP5/PP2A) provide further
insight into inhibitory actions of fostriecin family inhibitors, J.
Pharmacol. Exp. Ther. 2009, 331, 45-53.
479. K. S. MacMillan and D. L. Boger, Fundamental relationships between
structure, reactivity, and biological activity for the duocarmycins and
CC-1065, J. Med Chem. 2009, 52, 5771-5780.
478. S. G. Kinsey, J. Z. Long, S. T. O'Neal, R. A. Abdulla, J. L. Poklis,
D. L. Boger, B. F. Cravatt, and A. H. Lichtman, Blockade of
endocannabinoid-degrading enzymes attenuates neuropathic pain, J.
Pharmacol. Exp. Ther. 2009, 330, 902-910.
477. V. Subramanian, R. M. Williams, D. L. Boger, and K. Luger, Methods
to characterize the effect of DNA-modifying compounds on nucleosomal DNA,
in Methods in Molecular Biology, Vol. XXX: Drug-DNA Interactions 2nd Ed.,
Humana Press, Totowa, NJ, 2009, in press.
476. M. Mileni, J. Garfunkle, J. K. DeMartino, B. F. Cravatt, D. L.
Boger, and R. C. Stevens, Binding and inactivation mechanism of a
humanized fatty acid amide hydrolase by -ketoheterocycle inhibitors
revealed from co-crystal structures, J. Am. Chem. Soc. 2009,
131, 10497-10506.
475. L. R. Whitby, A. M. Lee, S. Kunz, M. B. A. Oldstone, and D. L.
Boger, Characterization of Lassa virus cell entry inhibitors:
determination of the active enantiomer by asymmetric synthesis, Bioorg.
Med. Chem. Lett. 2009, 19, 3771-3774.
Symposium-in-Print honoring C. Barbas, 2009 Tetrahedron Young Investigator
Award.
474. K. E. Hauschild, J. S. Stover, D. L. Boger, and A. Z. Ansari,
CSI-FID: high throughput label-free detection of DNA binding molecules, Bioorg.
Med. Chem. Lett. 2009, 19, 3779-3782.
Symposium-in-Print honoring C. Barbas, 2009 Tetrahedron Young Investigator
Award.
473. D. L. Boger and H. Ishikawa, Total synthesis of vindoline and
related alkaloids, J. Syn. Org. Chem., Jpn. 2009, 67,
123-133.
472. A. Shaginian, L. R. Whitby, S. Hong, I. Hwang, B. Faroogi, J. Chen,
M. Searcey, P. K. Vogt, and D. L. Boger, Design, synthesis, and evaluation
of an ?-helix mimetic library targeting protein-protein interactions, J.
Am. Chem. Soc. 2009, 131, 5564-5572.
471. C. M. Gauss, A. Hamasaki, J. P. Parrish, K. S. MacMillan, T. J.
Rayl, I. Hwang, and D. L. Boger, Synthesis and preliminary evaluation of
duocarmycin analogues incorporating the 1,2,11,11a-tetrahydrocyclopropa
[c]naphtho[2,3-e]indol-4-one (CNI) and
1,2,11,11a-tetrahydrocyclopropa[c]naphtho[1,2-e]indol-4-one (iso-CNI)
alkylation subunits, Tetrahedron 2009, 65,
6591-6599. Symposium-in-Print honoring L. Overman, 2009 Tetrahedron Award.
470. J. E. Schlosburg, D. L. Boger, B. F. Cravatt, and A. H. Lichtman,
Endocannabinoid modulation of scratching response in an acute allergenic
model: new prospective neural therapeutic target for pruritus, J.
Pharmacol. Exp. Ther. 2009, 329, 314-323.
469. H. Ishikawa, D. A. Colby, S. Seto, P. Va, A. Tam, H. Kakei, T. J.
Rayl, I. Hwang, and D. L. Boger, Total synthesis of vinblastine,
vincristine, related natural products and key structural analogues, J.
Am. Chem. Soc. 2009, 131, 4904-4916.
468. R. C. Clark, S. Y. Lee, I. Hwang, M. Searcey, and D. L. Boger,
Evaluation of chlorofusin, its seven chromophore diastereomers, and key
analogues, Tetrahedron Lett. 2009, 50, 3151-3153.
Symposium-in-Print commemorating the 50th Anniversary of Tetrahedron
Letters.
467. C. M. Crane and D. L. Boger, Synthesis and evaluation of vancomycin
aglycon analogues that bear modifications in the N-terminus D-leucyl amino
acid, J. Med. Chem. 2009, 52, 1471-1476.
466. J. S. Stover, J. Shi, W. Jin, P. K. Vogt, and D. L. Boger, Discovery
of inhibitors of aberrant gene transcription from libraries of DNA binding
molecules: inhibition of LEF-1 mediated gene transcription and oncogenic
transformation, J. Am. Chem. Soc. 2009, 131,
3342-3348.
465. R. C. Clark, S. Y. Lee, M. Searcey, and D. L. Boger, The isolation,
total synthesis and structure elucidation of chlorofusin, a natural
product inhibitor of the p53-MDM2 protein-protein interaction, Natural
Prod. Rep. 2009, 26, 465-477.
464. K. S. MacMillan, T. Nguyen, I. Hwang, and D. L. Boger, Total
synthesis and evaluation of iso-duocarmycin SA and iso-yatakemycin, J.
Am. Chem. Soc. 2009, 131, 1187-1194.
463. S. Y. Lee and D. L. Boger, Synthesis of the chlorofusin cyclic
peptide, Tetrahedron 2009, 65, 3281-3284.
Symposium-in-Print in honor of Justin Du Bois, 2008 Tetrahedron Young
Investigator Award.
462. J. K. DeMartino and D. L. Boger, Glycinamide ribonucleotide
transformylase (GAR Tfase) as a target for cancer therapy, Drugs Fut.
2008, 33, 969–979.
461. K. S. MacMillan and
D. L. Boger, An alternative spirocyclization for duocarmycin SA, J.
Am. Chem. Soc. 2008, 130, 16521–16523.
460. J. K. DeMartino, I.
Hwang, S. Connolly, I. A. Wilson, and D. L. Boger, Asymmetric synthesis
of inhibitors of glycinamide ribonucleotide transformylase, J. Med.
Chem. 2008, 51, 5441–5448.
459. J. K. DeMartino, J. Garfunkle, D. G. Hochstatter, B. F. Cravatt, and
D. L. Boger, Exploration of a fundamental substituent effect of
a-ketoheterocycle enzyme inhibitors: potent and selective inhibitors of
fatty acid amide hydrolase, Bioorg. Med. Chem. Lett. 2008,
18, 5842–5846. Symposium-in-print honoring B. F. Cravatt, 2008
Tetrahedron Young Investigator Award.
458. I. Slaymaker, M. Bracey, M. Mileni, J. Garfunkle, B. F. Cravatt, D.
L. Boger, and R. C. Stevens, Correlation of inhibitor effects on enzyme
activity and thermal stability for the integral membrane protein fatty
acid amide hydrolase, Bioorg. Med. Chem. Lett. 2008, 18,
5847–5850. Symposium-in-print honoring B. F. Cravatt, 2008 Tetrahedron
Young Investigator Award.
457. A. M. Lee, J. M.
Rojek, C. F. Spiropoulou, A. Gunderson, W. Jin, A. Shaginian, J. York,
J. H. Nunberg, D. L. Boger, M. B. A. Oldstone, and S. Kunz, Unique small
molecule entry inhibitors of hemorrahagic fever arenaviruses, J.
Biol. Chem. 2008, 283, 18734–18742.
456.R. C. Clark, S. Y. Lee,
and D. L. Boger, Total synthesis of chlorofusin, its seven chromophore
diastereomers, and key partial structures, J. Am. Chem. Soc. 2008,
130, 12355–12369.
455. J. Garfunkle, C.
Ezzili, T. J. Rayl, D. G. Hochstatter, I. Hwang, and D. L. Boger,
Optimization of the central heterocycle of a-ketoheterocycle inhibitors
of fatty acid amide hydrolase, J. Med. Chem. 2008, 51,
4392–4403.
454. X. Lu, P. K.
Vogt, D. L. Boger, and J. Lunec, Disruption of the MYC transcriptional
function by a small molecule antagonist of Myc/Max dimerization, Oncol.
Rep. 2008, 19, 825–830.
453. S. Di Micco, D.
L. Boger, R. Riccio, and G. Bifulco, Structural features of the
(+)-yatakemycin–d(GACTAATTGAC)-(GTCAATTAGTC) complex. Quantum mechanical
calculation of NMR parameters as a tool for the characterization of
ligand-DNA interactions, Eur. J. Org. Chem. 2008,
2454–2462.
452. H. Ishikawa, D. A.
Colby, and D. L. Boger, Direct Coupling of catharanthine and vindoline
to provide vinblastine: total synthesis of (+)- and ent-(-)-vinblastine,
J. Am. Chem. Soc. 2008, 130, 420–421.
451. F. S. Kimball, F. A.
Romero, C. Ezzili, J. Garfunkle, T. J. Rayl, D. G. Hochstatter, I.
Hwang, and D. L. Boger, Optimization of ?-ketooxazole inhibitors of
fatty acid amide hydrolase, J. Med. Chem. 2008, 51,
937–947.
450. M. S. Tichenor and D.
L. Boger, Yatakemycin: total synthesis, DNA alkylation, and biological
properties, Natural Prod. Rep. 2008, 25,
220–226.
449. W. Jin, J. D.
Trzupek, T. J. Rayl, M. A. Broward, G. A. Vielhauer, S. J. Weir, I.
Hwang, and D. L. Boger, A unique class of duocarmycin and CC-1065
analogues subject to reductive activation, J. Am. Chem. Soc. 2007,
129, 15391–15397.
448. M. S. Tichenor, K. S.
MacMillan, J. S. Stover, S. E. Wolkenberg, M. G. Pavani, L. Zanella, A.
N. Zaid, G. Spalluto, T. J. Rayl, I. Hwang, P. G. Baraldi, and D. L.
Boger, Rational design, synthesis, and evaluation of key analogues of
CC-1065 and the duocarmycins, J. Am. Chem. Soc. 2007, 129,
14092–14099.
447. M. S. Tichenor, K. S.
MacMillan, J. D. Trzupek, T. J. Rayl, I. Hwang, and D. L. Boger,
Systematic exploration of the structural features of yatakemycin
impacting DNA alkylation and biological activity, J. Am. Chem. Soc.
2007, 129, 10858–10869.
446. S. Y. Lee, R. C.
Clark, and D. L. Boger, Total synthesis, stereochemical reassignment,
and absolute configuration of chlorofusin, J. Am. Chem. Soc. 2007,
129, 9860–9861.
445. L. Xu, Y. Chong,
I. Hwang, A. D’Onofrio, K. Amore, G. P. Beardsley, C. Li, A. J. Olson,
D. L. Boger, and I. A. Wilson, Structure-based design, synthesis,
evaluation, and crystal structures of transition state analogue
inhibitors of inosine monophosphate cyclohydrolase, J. Biol. Chem.
2007, 282, 13033–13046.
444. J. Nam, D. Shin, Y.
Rew, and D. L. Boger, Alanine scan of [L-Dap2]ramoplanin A2 aglycon:
assessment of the importance of each residue, J. Am. Chem. Soc.
2007, 129, 8747–8755.
443. C. Hardouin, M. J.
Kelso, F. A. Romero, T. J. Rayl, D. Leung, I. Hwang, B. F. Cravatt, and
D. L. Boger, Structure–activity relationships of the a-ketooxazole
inhibitors of fatty acid amide hydrolase, J. Med. Chem. 2007,
50, 3359–3368.
442. L. M. Eubanks,
M. S. Hixon, W. Jin, S. Hong, C. M. Clancy, W. H. Tepp, C. J. Malizio,
M. C. Goodnough, J. T. Barbieri, E. A. Johnson, D. L. Boger, T. J.
Dickerson, and K. D. Janda, High throughput identification of botulinum
neurotoxin A antagonists: an in vitro and in vivo disconnect, Proc.
Natl. Acad. Sci. U.S.A. 2007, 104, 2602–2607
441. F. A. Romero, W. Du,
I. Hwang, T. J. Rayl, F. S. Kimball, D. Leung, H. S. Hoover, R. L.
Apodaca, J. G. Breitenbucher, B. F. Cravatt, and D. L. Boger, Potent and
selective a-ketoheterocycle-based inhibitors of the anandamide and
oleamide catabolizing enzyme, fatty acid amide hydrolase, J. Med.
Chem. 2007, 50, 1058–1068.
440. H. Ishikawa and D. L. Boger, Total synthesis of (–)- and
ent-(+)-4-desacetoxy-5-desethylvindoline, Heterocycles 2007,
72, 95–102. Commemorative issue honoring Y. Kishi on his 70th
birthday.
439. B. G. Lawhorn, S. B.
Boga, S. E. Wolkenberg, D. A. Colby, C.-M. Gauss, M. R. Swingle, L.
Amable, R. E. Honkanen, and D. L. Boger, Total synthesis of cytostatin,
its C10–C11 diastereomers and additional key analogues: impact on PP2A
inhibition, J. Am. Chem. Soc. 2006, 129,
16720–16732.
438. M. S. Tichenor, J. D.
Trzupek, D. B. Kastrinsky, F. Shiga, I. Hwang, and D. L. Boger,
Asymmetric total synthesis of (+)- and ent-(–)-yatakemycin and
duocarmycin SA: evaluation of yatakemycin key partial structures and its
unnatural enantiomer, J. Am. Chem. Soc. 2006, 128,
15683–15696.
437. F. A. Romero, I.
Hwang, and D. L. Boger, Delineation of a fundamental a-ketoheterocycle
substituent effect for use in the design of enzyme inhibitors, J.
Am. Chem. Soc. 2006, 128, 14004–14005.
436. B. G. Lawhorn, S. B. Boga, S. E. Wolkenberg, and D. L. Boger, Total
synthesis of cytostatin, Heterocycles 2006, 70,
65–70. Commemorative issue honoring S. Weinreb on his 65th
birthday.
435. M. J. Schnermann, F.
A. Romero, I. Hwang, E. Nakamaru-Ogiso, T. Yagi, and D. L. Boger, Total
synthesis of piericidin A1 and B1 and key analogues, J. Am. Chem.
Soc. 2006, 128, 11799–11807.
434. H. Ishikawa, G. I.
Elliott, J. Velcicky, Y. Choi, and D. L. Boger, Total synthesis of (–)-
and ent-(+)-vindoline and related alkaloids, J. Am. Chem.
Soc. 2006, 128, 10596–10612.
433. G. I. Elliott, J. R.
Fuchs, B. S. J. Blagg, H. Ishikawa, H. Tao, Z.-Q. Yuan, and D. L. Boger,
Intramolecular Diels–Alder/1,3-dipolar cycloaddition cascade of
1,3,4-oxadiazoles, J. Am. Chem. Soc. 2006, 128,
10589–10595.
432. J. K. DeMartino, I.
Hwang, L. Xu, I. A. Wilson, and D. L. Boger, Discovery of a potent,
non-polyglutamatable inhibitor of glycinamide ribonucleotide
transformylase, J. Med. Chem. 2006, 49,
2998–3002.
431. B. M. Crowley and D.
L. Boger, Total synthesis and evaluation of [Ψ(CH2NH)Tpg4]vancomycin
aglycon: reengineering vancomycin for dual D-Ala-D-Ala and D-Ala-D-Lac
binding, J. Am. Chem. Soc. 2006, 128, 2885–2892.
430. R. C. Clark, S. S.
Pfeiffer, and D. L. Boger, Diastereoselective Diels–Alder reactions of
N-sulfonyl-1-aza-1,3-butadienes with optically active enol ethers: an
asymmetric variant of the 1-azabutadiene Diels–Alder reaction, J.
Am. Chem. Soc. 2006, 128, 2587–2593.
429. X. Fang, K. Tiyanont,
Y. Zhang, J. Wanner, D. L. Boger, and S. Walker, The mechanism of action
of ramoplanin and enduracidin, Mol. BioSystems 2006, 2,
69–76.
428. J. D. Trzupek, J.
M. Gottesfeld, and D. L. Boger, Sequence-selective alkylation of duplex
DNA in nucleosome core particles with duocarmycin SA and yatakemycin, Nature
Chem. Biol. 2006, 2, 79–82.
427. A. Hamasaki, R.
Ducray, and D. L. Boger, Two novel 1,2,4,5-tetrazines that participate
in inverse electron demand Diels–Alder reactions with an unexpected
regioselectivity, J. Org. Chem. 2006, 71,
185–193.
426. G. I. Elliott,
J. Velcicky, H. Ishikawa, Y. Li, and D. L. Boger, Total synthesis of
(–)- and ent-(+)-vindorosine: tandem intramolecular
Diels–Alder/1,3-dipolar cycloaddition of 1,3,4-oxadiazoles, Angew.
Chem. Int. Ed. 2006, 45, 620–622.
425. C. R. W. Guimarăes,
D. L. Boger, and W. L Jorgensen, Elucidation of fatty acid amide
hydrolase inhibition by potent a-ketoheterocycle
derivatives from Monte Carlo simulations J. Am. Chem. Soc. 2005,
127, 17377–17384.
424. M. J. Schnermann and
D. L. Boger, Total synthesis of piercidin A1 and B1 J. Am. Chem.
Soc. 2005, 127, 15704–15705.
423. Y. Choi, H. Ishikawa,
J. Velcicky, G. I. Elliott, M. M. Miller, and D. L. Boger, Total
synthesis of (–)- and ent-(+)-vindoline Org. Lett. 2005,
7, 4539–4542.
422. A. Hamasaki, J. M.
Zimpleman, I. Hwang, and D. L. Boger, Total synthesis of ningalin D J.
Am. Chem. Soc. 2005, 127, 10767–10770.
421. K. J. Capps,
J. Humiston, R. Dominique, I. Hwang, and D. L. Boger, Discovery of a new
class of AICAR Tfase inhibitors that disrupt requisite enzyme
dimerization Bioorg. Med. Chem. Lett. 2005, 15,
2840–2844.
420. Z. Yuan, H. Ishikawa,
and D. L. Boger, Total synthesis of natural (+)- and ent-(–)-4-desacetoxy-6,7-dihydrovindorosine
and natural and ent-minovine: oxadiazole tandem intramolecular
Diels–Alder/1,3-dipolar cycloaddition reaction Org. Lett. 2005,
7, 741–745. Correction:
Org. Lett. 2005, 7, 2079.
419. T. -C. Chou,
Y. Guan, D. R. Soenen, S. J. Danishefsky, and D. L. Boger, Potent
reversal of multidrug resistance by ningalin and its use in drug
combinations against human colon carcinoma xenografts in nude mice Cancer
Chemother. Pharmacol. 2005, 56, 379–390.
418. D. Leung, W.
Du, C. Hardouin, H. Cheng, I. Hwang, B. F. Cravatt, and D. L. Boger,
Discovery of a class of exceptionally potent and selective inhibitors of
fatty acid amide hydrolase enlisting proteome-wide selectivity
screening: concurrent optimization of an enzyme inhibitor potency and
selectivity Bioorg. Med. Chem. Lett. 2005, 15,
1423–1428.
417. H. Cheng, I.
Hwang, Y. Chong, A. Tavassoli, M. E. Webb, Y. Zhang, I. A. Wilson, S. J.
Benkovic, and D. L. Boger, Synthesis and biological evaluation of
N-{4-[5-(2,4-diamino-6-oxo-1,6-dihydropyrimidin-5-yl)-2-(2,2,2-trifluoroacetyl)pentyl]benzoyl}-L-glutamate
as a potential inhibitor of GAR Tfase and the de novo purine
biosynthetic pathway Bioorg. Med. Chem. 2005, 13,
3593–3599.
416. Y. Chong, I.
Hwang, A. Tavassoli, Y. Zhang, I. A. Wilson, S. J. Benkovic, and D. L.
Boger, Synthesis and biological evaluation of a-
and g-carboxamide derivatives of 10-CF3CO-DDACTHF
Bioorg. Med. Chem. 2005, 13, 3587–3592.
415. H. Cheng, Y.
Chong, I. Hwang, A. Tavassoli, Y. Zhang, I. A. Wilson, S. J. Benkovic,
and D. L. Boger, Design, synthesis, and evaluation of
10-methanesulfonyl-DDACTHF, 10-methanesulfonyl-5-DACTHF, and
10-methylthio-DDACTHF as potent inhibitors of GAR Tfase and the de novo
purine biosynthetic pathway Bioorg. Med. Chem. 2005, 13,
3577–3585.
414. W. C. Tse and D. L. Boger, A fluorescent intercalator displacement
(FID) assay for establishing DNA binding selectivity and affinity Curr.
Protocols Nucleic Acid Chem. 2005, in press.
413. S. Walker, J. Helm,
Y. Hu, L. Chen, Y. Rew, D. Shin, and D. L. Boger, Chemistry and biology
of ramoplanin: a lipoglycodepsipeptide with potent antibiotic activity Chem.
Rev. 2005, 105, 449–476.
412. D. L. Boger, H.
Miyauchi, W. Du, C. Hardouin, R. A. Fecik, H. Cheng, I. Hwang, M. P.
Hedrick, D. Leung, O. Acevedo, C. R. W. Guimarăes, W. L. Jorgensen, and
B. F. Cravatt, Discovery of a potent, selective, and efficacious class
of reversible a-ketoheterocycle inhibitors
of fatty acid amide hydrolase effective as analgesics J. Med. Chem.
2005, 48, 1849–1856. (Paul Janssen Memorial Issue)
411. W. Du, C.
Hardouin, H. Cheng, I. Hwang, and D. L. Boger, Heterocyclic sulfoxide
and sulfone inhibitors of fatty acid amide hydrolase Bioorg. Med.
Chem. Lett. 2005, 15, 103–106.
410. H. Tao, I.
Hwang, and D. L. Boger, Multidrug resistance reversal activity of
permethyl ningalin B amide derivatives, Bioorg. Med. Chem. Lett.
2004, 14, 5979–5981.
409. J. P.
Parrish, J. D. Trzupek, T. V. Hughes, I. Hwang, and D. L. Boger,
Synthesis and evaluation of N-aryl and N-alkenyl CBI derivatives, Bioorg.
Med. Chem. 2004, 12, 5845–5856.
408. A. H. Lichtman,
D. Leung, C. C. Shelton, A. Saghatelian, C. Hardouin, D. L. Boger, and
B. F. Cravatt, Reversible inhibitors of fatty acid amide hydrolase that
promote analgesia: evidence for an unprecedented combination of potency
and selectivity, J. Pharmacol. Exp. Ther. 2004, 311,
441–448.
407. Y. -W. Ham and D. L.
Boger, A powerful selection assay for mixture libraries of DNA
alkylating agents, J. Am. Chem. Soc. 2004, 126,
9194–9195.
406. M. S. Tichenor, D. B.
Kastrinsky, and D. L. Boger, Total synthesis, structure revision, and
absolute configuration of (+)-yatakemycin, J. Am. Chem. Soc. 2004,
126, 8396–8398.
405. P. S. Lee, W. Du, D.
L. Boger, and W. L. Jorgensen, Energetic preferences for a,b
versus b,g
unsaturation, J. Org. Chem. 2004, 69, 5448–5453.
404. L. Chen, Y. Yuan, J.
S. Helm, Y. Hu, Y. Rew, D. Shin, D. L. Boger, and S. Walker, Dissecting
ramoplanin: mechanistic analysis of synthetic ramoplanin analogues as a
guide to the design of improved antibiotics, J. Am. Chem. Soc. 2004,
126, 7462–7463.
403. D. Shin, Y.
Rew, and D. L. Boger, Total synthesis and structure of the ramoplanin A1
and A3 aglycons: two minor components of the ramoplanin complex, Proc.
Natl. Acad. Sci. U.S.A. 2004, 101, 11977–11979.
402. A. M.
Lillo, C. Sun, C. Gao, H. Ditzel, J. Parrish, C.-M. Gauss, J. Moss, B.
Felding-Habermann, P. Wirsching, D. L. Boger and K. D. Janda, A human
single-chain antibody specific for integrin a3b1
capable of cell internalization and delivery of antitumor agents, Chem.
Biol. 2004, 11, 897–906.
401. B. M. Crowley, Y.
Mori, C. C. McComas, D. Tang, and D. L. Boger, Total synthesis of the
ristocetin aglycon, J. Am. Chem. Soc. 2004, 126,
4310–4317.
400. D. B. Kastrinsky and
D. L. Boger, Effective asymmetric synthesis of CBI, J. Org. Chem.
2004, 69, 2284–2289.
399. Y. Rew, D. Shin, I.
Hwang, and D. L. Boger, Total synthesis and examination of three key
analogues of ramoplanin: a lipoglycodepsipeptide with potent antibiotic
activity, J. Am. Chem. Soc. 2004, 126,
1041–1043.
398. J. P. Parrish, T. V.
Hughes, I. Hwang, and D. L. Boger, Establishing the parabolic
relationship between reactivity and activity for derivatives and
analogues of the duocarmycin and CC-1065 alkylation subunits, J. Am.
Chem. Soc. 2004, 126, 80–81.
397. W. C. Tse and D. L.
Boger, A fluorescent intercalator displacement (FID) assay for
establishing DNA binding selectivity and affinity, Acc. Chem. Res.
2004, 37, 61–69.
396. W. C.
Tse and D. L. Boger, Sequence-selective DNA recognition: natural
products and nature’s lessons, Chem. Biol. 2004, 11,
1607–1617.
395. P. Desai, S. S.
Pfeiffer, and D. L. Boger, Synthesis of the chlorofusin cyclic peptide:
assignment of Asn stereochemistry, Org. Lett. 2003, 5,
5047–5050.
394. S. B. Buck, C.
Hardouin, S. Ichikawa, D. R. Soenen, C.-M. Gauss, I. Hwang, M. R.
Swingle, K. M. Bonness, R. E. Honkanen, and D. L. Boger, Fundamental
role of the fostriecin unsaturated lactone and implications for
selective protein phosphatase inhibition, J. Am. Chem. Soc. 2003,
125, 15694–15695.
393. C. Bassarello,
P. Cimino, G. Bifulco, D. L. Boger, J. A. Smith, W. J. Chazin, and L. G.
Paloma, NMR structure of the
(+)-CPI-indole/d(GACTAATTGAC)-d(GTCAATTAGTC) covalent complex, ChemBioChem
2003, 4, 1188–1193.
392. J. P. Parrish, D. B.
Kastrinsky, Inkyu Hwang, and D. L. Boger, Synthesis and evaluation of
duocarmycin and CC-1065 analogues incorporating the
1,2,9,9a-tetrahydro-cyclopropa[c]benz[e]-3-azaindole-4-one
(CBA) alkylation subunit, J. Org. Chem. 2003, 68,
8984–8990.
391. W. C.
Tse, T. Ishii, and D. L. Boger, Comprehensive high resolution analysis
of hairpin polyamides utilizing a fluorescent intercalator displacement
(FID) assay, Bioorg. Med. Chem. 2003, 11,
4479–4486.
390. Y.-W. Ham,
W. C. Tse, and D. L. Boger, High resolution assessment of protein DNA
binding affinity and selectivity utilizing a fluorescent intercalator
displacement (FID) assay, Bioorg. Med. Chem. Lett. 2003,
13, 3805–3807.
389. B. K. S.
Yeung, W. C. Tse, and D. L. Boger, Determination of binding affinities
of triplex forming oligonucleotides using a fluorescent intercalator
displacement (FID) assay, Bioorg. Med. Chem. Lett. 2003,
13, 3801–3804.
388. J. P. Parrish, D. B.
Kastrinsky, S. E. Wolkenberg, Y. Igarashi, and D. L. Boger, DNA
alkylation properties of yatakemycin, J. Am. Chem. Soc. 2003,
125, 10971–10976.
387. C. C. McComas, B. M.
Crowley, and D. L. Boger, Partitioning the loss in vancomycin binding
affinity for D-Ala-D-Lac into lost H-bond and repulsive lone pair
contributions, J. Am. Chem. Soc. 2003, 125,
9314–9315.
386. J. P. Parrish, D. B.
Kastrinsky, and D. L. Boger, Synthesis and x-ray analysis of an
unprecedented and stable 2-aza-4,4-spirocyclopropacyclohexadienone, Org.
Lett. 2003, 5, 2577–2579.
385. B. K. S. Yeung and D.
L. Boger, Synthesis of isochrysohermidin–distamycin hybrids, J. Org.
Chem. 2003, 68, 5249–5253.
384. C. C.
McComas, B. M. Crowley, I. Hwang, and D. L. Boger, Synthesis and
evaluation of methyl ether derivatives of the vancomycin, teicoplanin,
and ristocetin aglycon methyl ethers, Bioorg. Med. Chem. Lett. 2003,
13, 2933–2936. Symposium-in-print: Recent Advances in
Antibiotics.
383. D. L. Boger, J.
Desharnais, and K. Capps, Solution-phase combinatorial libraries:
modulating cellular signaling by targeting protein–protein or
protein–DNA interactions, Angew. Chem. Int. Ed. 2003, 42,
4138–4176.
382. J.
Desharnais, I. Hwang, Y. Zhang, A. Tavassoli, J. Baboval, S. J.
Benkovic, I. A. Wilson, and D. L. Boger, Design, synthesis, and
biological evaluation of 10-CF3CO-DDACTHF analogues and
derivatives as inhibitors of GAR Tfase and the de novo purine
biosynthetic pathway, Bioorg. Med. Chem. 2003, 11,
4511–4521.
381. T. H.
Marsilje, M. P. Hedrick, J. Desharnais, K. Capps, A. Tavassoli, Y.
Zhang, I. A. Wilson, S. J. Benkovic, and D. L. Boger,
10-(2-Benzoxazolcarbonyl)-5,10-dideaza-acyclic-5,6,7,8-tetrahydrofolic
acid: a potential inhibitor of GAR transformylase and AICAR
transformylase, Bioorg. Med. Chem. 2003, 11,
4503–4509.
380. T. H.
Marsilje, M. P. Hedrick, J. Desharnais, A. Tavassoli, Y. Zhang, I. A.
Wilson, S. J. Benkovic, and D. L. Boger, Design, synthesis, and
biological evaluation of simplified a-keto
heterocycle, trifluoromethyl ketone, and formyl substituted folate
analogues as potential inhibitors of GAR transformylase and AICAR
transformylase, Bioorg. Med. Chem. 2003, 11,
4487–4501.
379. P. J.
Krenitsky and D. L. Boger, Synthesis of the (S,S,S)-diastereomer
of the 15-membered biaryl ring system of RP 66453, Tetrahedron Lett.
2003, 44, 4019–4022.
378. J. P.
Parrish, D. Kastrinsky, F. Stauffer, M. P. Hedrick, I. Hwang, and D. L.
Boger, Establishment of substituent effects in the DNA binding subunit
of CBI analogues of the duocarmycins and CC-1065, Bioorg. Med. Chem.
2003, 11, 3815–3838.
377. Y. Zhang, J.
Desharnais, T. H. Marsilje, C. Li, M. P. Hedrick, L. T. Gooljarsingh, A.
Tavassoli, S. J. Benkovic, A. J. Olson, D. L. Boger, and I. A. Wilson,
Rational design, synthesis, evaluation, and crystal structure of a
potent inhibitor of human GAR Tfase:
10-trifluoroacetyl-5,10-dideaza-acylic-5,6,7,8-tetrahydrofolic acid, Biochemistry
2003, 42, 6043–6056.
376. D. R.
Soenen, I. Hwang, M. P. Hedrick, and D. L. Boger, Multidrug resistant
reversal activity of key ningalin analogues, Bioorg. Med. Chem.
Lett. 2003, 13, 1777–1781.
375. D. Leung, C. Hardouin,
D. L. Boger, and B. F. Cravatt, Discovering potent and selective
reversible inhibitors of enzymes in complex proteomes, Nature
Biotechnol. 2003, 21, 687–691.
374. D. R. Soenen, J. M.
Zimpleman, and D. L. Boger, Synthesis and inverse electron demand
Diels–Alder reactions of
3,6-bis(3,4-dimethoxybenzoyl)-1,2,4,5-tetrazine, J. Org. Chem. 2003,
68, 3593–3598.
373. J.
Wanner, D. Tang, C. C. McComas, B. M. Crowley, W. Jiang, and D. L.
Boger, A new and improved method for deglycosidation of glycopeptide
antibiotics exemplified with vancomycin, ristocetin, and ramoplanin, Bioorg.
Med. Chem. Lett. 2003, 13, 1169–1173.
372. D. L.
Boger, Solution-phase synthesis of combinatorial libraries designed to
modulate protein–protein or protein–DNA interactions, Bioorg. Med.
Chem. 2003, 11, 1607–1613. Invited Perspectives
article.
371. W. Jiang, J. Wanner,
R. J. Lee, P.-Y. Bounaud, and D. L. Boger, Total synthesis of the
ramoplanin A2 and ramoplanose aglycon, J. Am. Chem. Soc. 2003,
125, 1877–1887.
370. D. L. Boger and S. L. Castle, Synthesis of cycloisodityrosine
peptides, Houben-Weyl, Methods of Organic Chemistry: Synthesis of
Peptides and Peptidomimetics; Goodman, M., Ed.; Theime: Stuttgart, 2002,
194-206.
369. Y. Zhang, J.
Desharnais, S. E. Greasley, G. P. Beardsley, D. L. Boger, and I. A.
Wilson, Crystal structures of human GAR Tfase at low and high pH and
with substrate b-GAR, Biochemistry 2002,
41, 14206-14215.
368. Y.
Ambroise, B. Yuspan, M. H. Ginsberg, and D. L. Boger, Inhibitors of cell
migration that inhibit intracellular Paxillin/a4
binding: a well documented use of positional scanning libraries, Chem.
Biol. 2002, 9, 1219-1226.
367. S. E. Wolkenberg and
Dale L. Boger, Total synthesis of anhydrolycorinone utilizing sequential
intramolecular Diels-Alder reactions of a 1,3,4-oxadiazole, J. Org.
Chem. 2002, 67, 7361-7364.
366. G. D. Wilkie, G. I.
Elliott, B. S. J. Blagg, S. E. Wolkenberg, D. R. Soenen, M. M. Miller,
S. Pollack, and D. L. Boger, Intramolecular Diels-Alder and tandem
intramolecular Diels-Alder/1,3-dipolar cycloaddition reactions of
1,3,4-oxadiazoles, J. Am. Chem. Soc. 2002, 124,
11292-11294.
365. C. R. Woods, T.
Ishii, and D. L. Boger, Synthesis and DNA binding properties of
iminodiacetic acid (IDA) linked polyamides: characterization of
cooperative extended 2:1 side-by-side parallel binding, J. Am. Chem.
Soc. 2002, 124, 10676-10682.
364. C. R.
Woods, N. Faucher, B. Eschgfaller, K. W. Bair, and D. L. Boger,
Synthesis and DNA binding properties of saturated distamycin analogues,
Bioorg. Med. Chem. Lett. 2002, 12, 2647-2650.
363. B. S.
J. Blagg and D. L. Boger, Total synthesis of (+)-camptothecin, Tetrahedron
2002, 58, 6343-6349.
362. S. E. Wolkenberg and
D. L. Boger, Mechanisms of in situ activation of DNA targeting antitumor
agents, Chem. Rev. 2002, 102, 2477-2496.
361. Y. Chen, M. Bilban,
C. A. Foster, and D. L. Boger, Solution-phase parallel synthesis of a
pharmacophore library of HUN-7293 analogues: a general chemical
mutagenesis approach to defining structure-function properties of cyclic
(depsi)peptides, J. Am. Chem. Soc. 2002, 124,
5431-5440.
360. W. Jiang, J. Wanner,
R. J. Lee, P.-Y. Bounaud, and D. L. Boger, Total synthesis of the
ramoplanin A2 and ramoplanose aglycon, J. Am. Chem. Soc. 2002,
124, 5288-5290.
359. T. H.
Marsilje, M. A. Labroli, M. P. Hedrick. Q. Jin, J. Desharnais, S. J.
Baker, L. J. Gooljarsingh, J. Ramacharan, A. Tavassoli, Y. Zhang, I. A.
Wilson, G. P. Bearsley, S. J. Benkovic, and D. L. Boger,
10-Formyl-5,10-dideaza-acyclic-5,6,7,8-tetrahydrofolic acid
(10-Formyl-DDACTHF): a potent cytotoxic agent acting by selective
inhibition of human GAR Tfase and the de novo purine biosynthetic
pathway, Bioorg. Med. Chem. 2002, 10, 2739-2749.
358. J. J.
McAtee, S. L. Castle, Q. Jin, and D. L. Boger, Synthesis and evaluation
of vancomycin and vancomycin aglycon analogues which bear modifications
of the residue 3 asparagine, Bioorg. Med. Chem. Lett. 2002,
12, 1319-1322.
357. T. Berg, S. B.
Cohen, J. Desharnais, C. Sonderegger, D. J. Maslyar, J. Goldberg, D. L.
Boger, and P. K. Vogt, Small molecule antagonists of Myc/Max
dimerization in vitro inhibit Myc induced transformation of
chicken embryo fibroblasts, Proc. Natl. Acad. Sci. USA 2002,
99, 3830-3835.
356. C. R. Woods, T.
Ishii, B. Wu, K. W. Bair, and D. L. Boger, Hairpin versus extended DNA
binding of a substituted b-alanine linked
polyamide, J. Am. Chem. Soc. 2002, 124,
2148-2152.
355. J. Goldberg, Q. Jin,
Y. Ambroise, S. Satoh, J. Desharnais, K. Capps, and D. L. Boger,
Erythropoietin mimetics derived from solution phase combinatorial
libraries, J. Am. Chem. Soc. 2002, 124, 544-555.
354. Y.
Ambroise and D. L. Boger, The DNA phosphate backbone is not involved in
catalysis of the duocarmycin and CC-1065 DNA alkylation reaction, Bioorg.
Med. Chem. Lett. 2002, 12, 303-306.
353. P. J.
Krenitsky and D. L. Boger, Preparation of the 14-membered
L,L-cycloisodityrosine subunit of RP 66453, Tetrahedron Lett. 2002,
43, 407-410.
352. D. Lewy, C.-M. Gauss, and D. L. Boger, Fostriecin: chemistry and
biology, Curr. Med. Chem. 2002, 9, 2005-2032.
351. S. E. Greasley, T. H.
Marsilje, H. Cai, S. Baker, S. J. Benkovic, D. L. Boger, Unexpected
formation of an epoxide-derived multisubstrate adduct inhibitor on the
active site of GAR transformylase, Biochemistry 2001, 40,
13538-13547.
350. I. Fedorova, A. Hashimoto, R. A. Fecik, M. P. Hedrick, L. O. Hanus,
D. L. Boger, K. C. Rice, and A. S. Basile, Behavioral evidence for the
interaction of oleamide with multiple neurotransmitter systems, J.
Pharmacol. Exp. Ther. 2001, 299, 332-342.
349. D. L.
Boger and W. C. Tse, Thiazole orange as the fluorescent intercalator in
a high resolution fid assay for determining DNA binding affinity and
sequence selectivity of small molecules, Bioorg. Med. Chem. 2001,
9, 2511-2518.
348. D. L. Boger, H. W.
Schmitt, B. E. Fink, and M. P. Hedrick, Parallel synthesis and
evaluation of 132 (+)-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one
(CBI) analogues of CC-1065 and the duocarmycins defining the
contribution of the DNA-binding domain, J. Org. Chem. 2001,
66, 6654-6661.
347. D. L. Boger,
Vancomycin, teicoplanin, and ramoplanin: synthetic and mechanistic
studies, Med. Res. Rev. 2001, 21, 356-381.
346. D. A. Ellis, S. E.
Wolkenberg, and D. L. Boger, Metal cation complexation and activation of
reversed CPyI analogues of CC-1065 and duocarmycin SA: partitioning the
effects of binding and catalysis, J. Am. Chem. Soc. 2001,
123, 9299-9306.
345. Y.
Mori, J. J. McAtee, O. Rogel, and D. L. Boger, Alternative synthesis and
thermal atropisomerism of a fully functionalized DEFG ring system of
teicoplanin, Tetrahedron Lett. 2001, 42,
6061-6064.
344. D. L. Boger and J.
Hong, Asymmetric total synthesis of ent-(-)-roseophilin:
assignment of absolute configuration, J. Am. Chem. Soc. 2001,
123, 8515-8519.
343. D. L.
Boger, F. Stauffer, and M. P. Hedrick, Substituent effects within the
DNA binding subunit of CBI analogues of the duocarmycins and CC-1065, Bioorg.
Med. Chem. Lett. 2001, 9, 2021-2024.
342. D. L. Boger, S. R.
Brunette, and R. M. Garbaccio, Synthesis and evaluation of a series of
C3-substituted CBI analogues of CC-1065 and the duocarmycins, J.
Org. Chem. 2001, 66, 5163-5173.
341. D. L.
Boger, H. Miyauchi, and M. P. Hedrick, a-Keto
heterocycle inhibitors of fatty acid amide hydrolase: carbonyl group
modification and a-substitution, Bioorg.
Med. Chem. Lett. 2001, 9, 1517-1520.
340. D. L. Boger, B. E.
Fink, S. R. Brunette, W. C. Tse, and M. P. Hedrick, A simple, high
resolution method for establishing DNA binding affinity and sequence
selectivity, J. Am. Chem. Soc. 2001, 123,
5878-5891.
339. D. L. Boger, S.
Ichikawa, and W. Zhong, Total synthesis of fostriecin (CI-920), J.
Am. Chem. Soc. 2001, 123, 4161-4167.
338. D. L. Boger, T. V.
Hughes, and M. P. Hedrick, Synthesis, chemical properties, and
biological evaluation of CC-1065 and duocarmycin analogues incorporating
the 5-methoxycarbonyl-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one
alkylation subunit, J. Org. Chem. 2001, 66,
2207-2216.
337. D. L. Boger, S. H.
Kim, Y. Mori, J.-H. Weng, O. Rogel, S. L. Castle, and J. J. McAtee,
First and second generation total synthesis of the teicoplanin aglycon,
J. Am. Chem. Soc. 2001, 123, 1862-1871.
336. D. L. Boger, J.
Goldberg, S. Silletti, T. Kessler, and D. A. Cheresh, Identification of
a novel class of small-molecule anti-angiogenic agents through screening
of combinatorial libraries which function by inhibiting the binding and
localization of proteinase MMP2 to integrin avb3,
J. Am. Chem. Soc. 2001, 123, 1280-1288.
335. D. L. Boger, S.
Ichikawa, W. C. Tse, M P. Hedrick, and Q. Jin, Total synthesis of
thiocoraline and BE-22179 and assessment of their DNA binding and
biological propertied, J. Am. Chem. Soc. 2001, 123,
561-568.
334. S. Siletti, T.
Kessler, J. Goldberg, D. L. Boger, and D. A. Cheresh, Disruption of MMP2
binding to integrin avb3
by a novel organic molecule inhibits angiogenesis and tumor growth in
vivo, Proc. Natl. Acad. Sci. USA 2001, 98,
119-124.
333. D. L.
Boger and J. Goldberg, Cytokine receptor dimerization and activation:
prospects or small molecule agonists, Bioorg. Med. Chem. 2001,
9, 557-562.
332. D. L. Boger, S.
Ichikawa, and H. Jiang, Total synthesis of the rubrolone aglycon, J.
Am. Chem. Soc. 2000, 122, 12169-122173.
331. D. L. Boger and S. E.
Wolkenberg, Total synthesis of Amaryllidaceae alkaloids
utilizing sequential intramolecular heterocyclic azadiene Diels-Alder
reactions of an unsymmetrical 1,2,4,5-tetrazine, J. Org. Chem. 2000,
65, 9120-9124.
330. D. L.
Boger, B. M. Aquila, W. C. Tse, and M. Searcey, Synthesis and evaluation
of a novel bleomycin A2 analogue: continuing assessment of the linker
domain, Tetrahedron Letters 2000, 41, 9493-9498.
329. D. L.
Boger, R. A. Fecik, J. E. Patterson, H. Miyauchi, M. P. Patricelli, and
B. F. Cravatt, Fatty acid amide hydrolase substrate specificity, Bioorg.
Med. Chem. Lett. 2000, 10, 2613-2616.
328. D. L. Boger, J.-H.
Weng, S. Miyazaki, J. J. McAtee, S. L. Castle, S. H. Kim, Y. Mori, O.
Rogel, H. Strittmatter, and Q. Jin, Thermal atropisomerism of
teicoplanin aglycon derivatives: preparation of the P,P,P and M,P,P
atropisomers of the teicoplanin aglycon via selective equilibration of
the DE ring system, J. Am. Chem. Soc. 2000, 122,
10047-10055.
327. J. A. Smith, G.
Bifulco, D. A. Case, D. L. Boger, L. Gomez-Paloma, and W. J. Chazin, J.
Mol. Biol. 2000, 300, 1195-1204.
326. D. L. Boger, R. J.
Lee, P.-Y. Bounaud, and P. Meier, Asymmetric synthesis of orthogonally
protected L-threo-b-hydroxyasparagine, J.
Org. Chem. 2000, 65, 6770-6772.
325. D. L. Boger and J. K.
Lee, Development of a solution-phase synthesis of minor groove binding
bis-intercalators based on triostin A suitable for combinatorial
synthesis, J. Org. Chem. 2000, 65, 5996-6000.
324. D. L.
Boger, M. A. Dechantsreiter, T. Ishii, B. E. Fink, and M. P. Hedrick,
Assessment of solution phase positional scanning libraries based on
distamycin A for the discovery of new DNA binding agents, Bioorg.
Med. Chem. 2000, 8, 2049-2057.
323. D. L.
Boger, Y. Chen, and C. A. Foster, Synthesis and evaluation of aza
HUN-7293, Bioorg. Med. Chem. Lett. 2000, 10,
1741-1744.
322. D.
L. Boger, J. Goldberg, S. Satoh, S. B. Cohen, and P. K. Vogt, Non
amide-based combinatorial libraries derived from N-BOC iminodiacetic
acid: solution-phase synthesis of a 150-membered piperazinone library
with activity against LEF-1/b-catenin
mediated transcription, Helv. Chim. Acta 2000, 83,
1825-1845.
321. D. L. Boger, S. H.
Kim, S. Miyazaki, H. Strittmatter, J.-H. Weng, Y. Mori, O. Rogel, S. L.
Castle, and J. J. McAtee, Total synthesis of the teicoplanin aglycon, J.
Am. Chem. Soc. 2000, 122, 7416-7417.
320. D. L. Boger, B. E.
Fink, and M. P. Hedrick, Total synthesis of distamycin A and 2640
analogs: a solution-phase combinatorial approach to the discovery of
new, bioactive DNA binding agents and development of a rapid,
high-throughput screen for determining relative DNA binding affinity or
DNA binding sequence selectivity, J. Am. Chem. Soc. 2000,
122, 6382-6394.
319. D. L. Boger, S. E.
Wolkenberg, and C. W. Boyce, A new method in situ activation for
a novel class of DNA alkylating agents: tunable metal cation
complexation and activation, J. Am. Chem. Soc. 2000, 122,
6325-6326.
318. D. L.
Boger, T. H. Marsilje, R. A. Castro, M. P. Hendrick, Q. Jin, S. J.
Baker, J. Shim, and S. J. Benkovic, Design, synthesis, and evaluation of
fluoronitrophenyl folate analogs as potential GAR transformylase and
AICAR transformylase inhibitors, Bioorg. Med. Chem. Lett. 2000,
10, 1471-1475.
317. D. L. Boger and J. Goldberg, Multi-step solution-phase combinatorial
chemistry, Chapter 10 in Combinatorial Chemistry: A Practical Approach,
Fenniri, H., Ed.; Oxford University Press: Oxford, 2000, 303-326.
316. D. L. Boger,
Solution-phase synthesis of combinatorial libraries: to bead or not to
bead, in perspective articles on the utility and application of
solution-phase combinatorial chemistry, C. M. Baldino, J.
Combinatorial Chem. 2000, 2, 89-103.
315. D. L. Boger, A.
Santillán, Jr., M. Searcey, S. R. Brunette, S. E. Wolkenberg, M. P.
Hedrick, and Q. Jin, Synthesis and evaluation of
1,2,8,8a-tetrahydrocyclopropo[c]pyrrolo[3,2-e]indol-4(5H)-one, the
parent alkylation subunit of CC-1065 and the duocarmycins: impact of the
alkylation subunit substituents and its implications for DNA alkylation
catalysis, J. Org. Chem. 2000, 65, 4101-4111.
314. D. L. Boger and C. W.
Boyce, Selective metal cation activation of a DNA alkylating agent:
synthesis and evaluation of methyl
1,2,9,9a-tetrahydrocyclopropa[c]pyrido[3,2-e]indol-4-one-7-carboxylate,
J. Org. Chem. 2000, 65, 4088-4100.
313. D. L.
Boger, B. E. Fink, and M. P. Hedrick, A new class of highly cytotoxic
diketopiperazines, Bioorg. Med. Chem. Lett. 2000, 10,
1019-1020.
312. D. L. Boger, H.
Sato, A. E. Lerner, M. P. Hedrick, R. A. Fecik, H. Miyauchi, G. D.
Wilkie, B. J. Austin, M. P. Patricelli, and B. F. Cravatt, Exceptionally
potent inhibitors of fatty acid amide hydrolase: the enzyme responsible
for degradation of endogenous oleamide and anandamide, Proc. Natl.
Acad. Sci. USA 2000, 97, 5044-5049.
311. D. L. Boger, D. R.
Soenen, C. W. Boyce, M. P. Hedrick, and Q. Jin, Total synthesis of
ningalin B utilizing a heterocyclic azadiene Diels-Alder reaction and
discovery of a new class of potent multidrug resistant (MDR) reversal
agents, J. Org. Chem. 2000, 65, 2479-2483.
310. D. L. Boger and S.
Ichikawa, Total syntheses of thiocoraline and BE-22179: establishment of
relative and absolute stereochemistry, J. Am. Chem. Soc. 2000,
122, 2956-2957.
309. D. L.
Boger, M. A. Labroli, T. H. Marsilje, Q. Jin, M. P. Hedrick, S. J.
Baker, J. H. Shim, and S. J. Benkovic, Conformationally restricted
analogs designed for selective inhibition of GAR Tfase versus
thymidylate synthase or dihydrofolate reductase, Bioorg. Med. Chem.
2000, 8, 1075-1086.
308. D. L.
Boger, M. Searcey, W. C. Tse, and Q. Jin, Bifunctional alkylating agents
derived from duocarmycin SA: potent antitumor activity with altered
sequence selectivity, Bioorg. Med. Chem. Lett. 2000, 10,
495-498.
307. D. L. Boger, J. K.
Lee, J. Goldberg, and Q. Jin, Two comparisons of the performance of
positional scanning and deletion synthesis for the identification of
active constituents in mixture combinatorial libraries, J. Org.
Chem. 2000, 65, 1467-1474.
306. P. G.
Baraldi, B. Cacciari, R. Romagnoli, G. Spalluto, C. W. Boyce, and D. L.
Boger, Resolution of a CPzI precursor. Synthesis and biological
evaluation of (+)- and (-)-Nboc-CPzI: a further validation of the
relationship between chemical solvolytic stability and cytotoxicity, Bioorg.
Med. Chem. Lett. 1999, 9, 3087-3092.
305. D. L. Boger and R. M.
Garbaccio, Shape-dependent catalysis: insights into the source of
catalysis for the CC-1065 and duocarmycin DNA alkylation reaction, Acc.
Chem. Res. 1999, 32, 1043-1052.
304. S. M. Greasley, M. M.
Yamashita, H. Cai, S. J. Benkovic, D. L. Boger, and I. A. Wilson, New
insights into inhibitor design from the crystal structure and NMR
studies of E. coli glycinamide ribonucleotide transformylase in
complex with ß-GAR and the inhibitor 10-formyl-5,8,10-trideazafolic
acid, Biochemistry 1999, 38, 16783-16793.
303. D. L. Boger, M. W.
Ledeboer, M. Kume, M. Searcey, and Q. Jin, Total synthesis and
comparative evaluation of luzopeptin A-C and quinoxapeptin A-C, J.
Am. Chem. Soc. 1999, 121, 11375-11383.
302. D. L. Boger, S.
Miyazaki, S. H. Kim, J. H. Wu, S. L. Castle, O. Loiseleur, and Q. Jin,
Total synthesis of the vancomycin aglycon, J. Am. Chem. Soc.
1999, 121, 10004-10011.
301. D. L. Boger and R. M.
Garbaccio, A novel class of CC-1065 and duocarmycin analogs subject to
mitomycin related reductive activation, J. Org. Chem. 1999,
64, 8350-8362.
300. D. L. Boger, W.
Jiang, and J. Goldberg, Convergent solution phase synthesis of
combinatorial libraries through rigid biaryl or diacetylene couplings, J.
Org. Chem. 1999, 64, 7094-7100.
299. D. L. Boger, C. W.
Boyce, R. M. Garbaccio, M. Searcey, and Q. Jin, CBI prodrug analogs of
CC- 1065 and the duocarmycins, Synthesis 1999, 1505-1509.
30th Anniversary Celebration issue, topic: Chemistry and Medicine.
298. D. L. Boger and R. M.
Garbaccio, Are the duocarmycin and CC-1065 DNA alkylation reactions
acid-catalyzed? Solvolysis pH rate profiles suggest they are not, J.
Org. Chem. 1999, 64, 5666-5669.
297. D. L. Boger, A.
Santillán, Jr., M. Searcey, and Q. Jin, Synthesis and evaluation of
duocarmycin and CC-1065 analogues containing modifications in the
subunit linking amide, J. Org. Chem. 1999, 64,
5241-5244.
296. D. L. Boger, H. Keim,
B. Oberhauser, E. P. Schreiner, and C. A. Foster, Total synthesis of
HUN-7293, J. Am. Chem. Soc. 1999, 121, 6197-6205.
295. J. R. Schnell, R. R.
Ketchem, D. L. Boger, and W. J. Chazin, DNA binding-induced alkylation:
insights from the structure of a DNA duplex alkylated by the indole
derivative of duocarmycin SA, J. Am. Chem. Soc. 1999,
121, 5645-5652.
294. D.
L. Boger, M. W. Ledeboer, M. Kume, and Q. Jin, Total synthesis of
quinoxapeptin A-C: establishment of absolute stereochemistry, Angew.
Chem , Int. Ed. 1999, 38, 2424-2426.
293. D. L.
Boger, H. Sato, A. E. Lerner, X. Guan, and N. B. Gilula, Arachidonic
acid amide inhibitors of gap junction cell-cell communication, Bioorg.
Med. Chem. Lett. 1999, 9, 1151-1154.
292. D. L. Boger, J.
Goldberg, and C.-M. Andersson, Solution phase combinatorial synthesis of
biaryl libraries employing heterogeneous conditions for catalysis and
isolation with size exclusion chromatography for purification, J.
Org. Chem. 1999, 64, 2422-2427.
291. B. J. Wilcox, K. J.
Ritenour-Rodgers, A. S. Asser, L. E. Baumgart, M. A. Baumgart, D. L.
Boger, J. E. Patterson, J. L. DeBlassio, M. A. deLong, U. Glufke, M. E.
Henz, L. King III, K. A. Merkler, J. J. Robleski, J. C. Vederas, and D.
J. Merkler, N-Acylglycine amidation: implications for the
biosynthesis of fatty acid primary amides, Biochemistry 1999,
38, 3235-3245.
290. D. L.
Boger and K. W. Saionz, DNA binding properties of key sandramycin
analogs: systematic examination of the intercalation chromophore, Bioorg.
Med. Chem. 1999, 7, 315-322.
289. D. L.
Boger, H. Sato, A. E. Lerner, B. J. Austin, J. E. Patterson, M. P.
Patricelli, and B. F. Cravatt, Trifluoromethyl ketone inhibitors of
fatty acid amide hydrolase: a probe of structural and conformational
features contributing to inhibition, Bioorg. Med. Chem. Lett. 1999,
9, 265-270.
288. D.
L. Boger and H. Cai, Bleomycin: synthetic and mechanistic studies, Angew.
Chem., Int. Ed. 1999, 38, 448-476.
287. D. L. Boger, S.
Miyazaki, S. H. Kim, J. H. Wu, O. Loiseleur, and S. L. Castle,
Diastereoselective total synthesis of the vancomycin aglycon with
ordered atropisomer equilibrations, J. Am. Chem. Soc. 1999,
121, 3226-3227.
286. D. L. Boger, J. Hong,
M. Hikota, and M. Ishida, Total synthesis of phomazarin, J. Am.
Chem. Soc. 1999, 121, 2471-2477.
285. D. L. Boger, M. W.
Ledeboer, and M. Kume, Total synthesis of luzopeptins A-C, J. Am.
Chem. Soc. 1999, 121, 1098-1099.
284. D. L. Boger, C. W.
Boyce, M. A. Labroli, C. A. Sehon, and Q. Jin, Total syntheses of
ningalin A, lamellarin O, lukianol A, and permethyl storniamide A
utilizing heterocyclic azadiene Diels-Alder reactions, J. Am. Chem.
Soc. 1999, 121, 54-62.
283. D. L. Boger, S. L.
Castle, S. Miyazaki, J. H. Wu, R. T. Beresis, and O. Loiseleur,
Vancomycin CD and DE macrocyclization and atropisomerism studies, J.
Org. Chem. 1999, 64, 70-80.
282. D. L. Boger and P.
Turnbull, Synthesis and evaluation of a carbocyclic analog of the
CC-1065 and duocarmycin alkylation subunits: role of the vinylogous
amide and implications on DNA alkylation catalysis, J. Org. Chem.
1998, 63, 8004-8011.
281. D. L. Boger, A.
Santillán, Jr., M. Searcey, and Q. Jin, The critical role of the linking
amide in CC-1065 and the duocarmycins: implications on the source of DNA
alkylation catalysis, J. Am. Chem. Soc. 1998, 120,
11554-11557.
280. D. L. Boger, T. M.
Ramsey, H. Cai, S. T. Hoehn, and J. Stubbe, Definition of the effect and
role of the bleomycin A2 valerate substituents:
preorganization of a rigid, compact conformation implicated in sequence
selective DNA cleavage, J. Am. Chem. Soc. 1998, 120,
9149-9158.
279. D. L. Boger, T. M.
Ramsey, H. Cai, S. T. Hoehn, and J. Stubbe, A systematic evaluation of
the bleomycin A2 L-threonine side chain: its role in
preorganization of a compact conformation implicated in sequence
selective DNA cleavage, J. Am. Chem. Soc. 1998, 120,
9139-9148.
278. D. L. Boger, S.
Miyazaki, O. Loiseleur, R. T. Beresis, S. L. Castle, J. H. Wu, and Q.
Jin, Thermal atropisomerism of aglucovancomycin derivatives: preparation
of (M,M,M)- and (P,M,M)-aglucovancomycin,
J. Am. Chem. Soc. 1998, 120, 8920-8926.
277. D. L.
Boger, J. Goldberg, W. Jiang, W. Chai, P. Ducray, J. K. Lee, R. S. Ozer,
and C.-M. Andersson, Higher order iminodiacetic acid libraries for
probing protein-protein interactions, Bioorg. Med. Chem. 1998,
6, 1347-1378. (Symposium-in-Print honoring S. Schreiber receipt
of Tetrahedron Prize).
276. D. L.
Boger, P. Ducray, W. Chai, W. Jiang, and J. Goldberg, Higher order
iminodiacetic acid libraries for probing protein-protein interactions, Bioorg.
Med. Chem. Lett. 1998, 8, 2339-2344.
(Symposium-in-Print on Combinatorial Chemistry).
275. D. L. Boger and G.
Schüle, Synthesis of acyclic precursors to (3S,4S)-4-hydroxy-2,3,4,5-tetrahydropyridazine-3-carboxylic
acid and incorporation into a luzopeptin/quinoxapeptin dipeptide, J.
Org. Chem. 1998, 63, 6421-6424.
274. D. L. Boger, R. P.
Schaum, and R. M. Garbaccio, Regioselective inverse electron demand
Diels-Alder reactions of N-acyl
6-amino-3-methylthio-1,2,4,5-tetrazines, J. Org. Chem. 1998,
63, 6329-6337.
273. D. L. Boger, W. Chai,
and Q. Jin, Multistep convergent solution-phase combinatorial synthesis
and deletion synthesis deconvolution, J. Am. Chem. Soc. 1998,
120, 7220-7225.
272. D. L. Boger, S. J. Henriksen, and B. F. Cravatt, Oleamide: An
endogenous sleep-inducing lipid and prototypical member of a new class of
biological signaling molecules, Current Pharmaceutical Design 1998,
4, 203-214.
271. D. L.
Boger, R. T. Beresis, O. Loiseleur, J. H. Wu, and S. L. Castle,
Synthesis of the vancomycin CDE ring system, Bioorg. Med. Chem.
Lett. 1998, 8, 721-724.
270. M. P.
Patricelli, J. E. Patterson, D. L. Boger, and B. F. Cravatt, An
endogenous REM sleep inducing compound is a potent competitive inhibitor
of fatty acid amide hydrolase (FAAH), Bioorg. Med. Chem. Lett. 1998,
8, 613-618.
269. D. L. Boger, J.
E. Patterson, X. Guan, B. F. Cravatt, R. A. Lerner, and N. B. Gilula,
Chemical requirements for inhibition of gap junction communication by
the biologically active lipid oleamide, Proc. Natl. Acad. Sci.
U.S.A. 1998, 95, 4810-4815.
268. D. L. Boger, J.
E. Patterson, and Q. Jin, Structural requirements for 5-HT2A
and 5-HT1A receptor potentiation by the biologically active
lipid oleamide, Proc. Natl. Acad. Sci. U.S.A. 1998,
95, 4102-4107.
267. D. L.
Boger and W. Chai, Solution-phase combinatorial synthesis: convergent
multiplication of diversity via the olefin metathesis reaction, Tetrahedron
1998, 54, 3955-3970. (Tetrahedron
Symposium-in-Print on solution-phase combinatorial synthesis).
266. D. L.
Boger, C. W. Boyce, R. M. Garbaccio, and M. Searcey, Synthesis of
CC-1065/duocarmycin analogs via intramolecular aryl radical cyclization
of a tethered vinyl chloride, Tetrahedron Letters 1998,
39, 2227-2230.
265. D. L. Boger, Heterocyclic and acyclic azadiene Diels-Alder
Reactions: total synthesis of nothapodytine B, J. Heterocyclic Chem.
1998, 35, 1003-1011. (Award Lecture, 1997 ISHC
Katritzky Award).
264. D. L.
Boger, M. J. Kochanny, H. Cai, D. Wyatt, P. A. Kitos, M. S. Warren, J.
Ramcharan, L. T. Gooljarsingh, and S. J. Benkovic, Design, synthesis,
and evaluation of potential GAR and AICAR inhibitors, Bioorg. Med.
Chem. 1998, 6, 643-659.
263. W. Wu, D. E.
Vanderwall, S. Teramoto, S. M. Lui, S. T. Hoehn, X.-J. Tang, C. J.
Turner, D. L. Boger, J. W. Kozarich, and J. Stubbe, NMR studies of Co
deglycobleomycin A2 green and its complex with
oligonucleotide d(CCAGGCCTGG)2, J. Am. Chem. Soc. 1998,
120, 2239-2250.
262. D. L. Boger and J.
Hong, Total synthesis of nothapodytine B and (-)mappicine, J. Am.
Chem. Soc., 1998, 120, 1218-1222.
261. T. M. Ramsey, H. Cai,
S. T. Hoehn, J. W. Kozarich, J. Stubbe, and D. L. Boger, Assessment of
the role of the bleomycin A2 pyrimidoblamic acid C4 amino
group, J. Am. Chem. Soc. 1998, 120,
53-65.
260. D. L.
Boger, J.-H. Chen, K. W. Saionz, and Q. Jin, Synthesis of key
sandramycin analogs: systematic examination of the intercalation
chromophore, Bioorg. Med. Chem. 1998, 6,
85-102.
259. D. L. Boger, R. M.
Garbaccio, and Q. Jin, Synthesis and evaluation of CC-1065 and
duocarmycin analogs incorporating the iso-CI and iso-CBI
alkylation subunits: impact of relocation of the C-4 carbonyl, J.
Org. Chem. 1997, 62, 8875-8891.
258. X. Guan, B. F.
Cravatt, G. R. Ehring, J. E. Hall, D. L. Boger, R. A. Lerner, and N. B.
Gilula, The sleep-inducing lipid oleamide deconvolutes Gap junction
communication and calcium wave transmission in glial cells, J. Cell
Biol. 1997, 139, 1785-1792.
257. D. L.
Boger, O. Loiseleur, S. L. Castle, R. T. Beresis, and J. H. Wu, Thermal
atropisomerism of fully functionalized vancomycin CD, DE, and CDE ring
systems, Bioorg. Med. Chem. Lett. 1997,
7, 3199-3202.
256. D. L. Boger and P.
Turnbull, Synthesis and evaluation of CC-1065 and duocarmycin analogs
incorporating the 1,2,3,4,11,11a-hexahydrocyclopropa[c]naphtho[2,1-b]azepin-6-one
(CNA) alkylation subunit: structural features that govern reactivity and
reaction regioselectivity, J. Org. Chem. 1997,
62, 5849-5863.
255. D. L.
Boger, R. S. Ozer, and C.-M. Andersson, Generation of symmetrical
compound libraries by solution-phase combinatorial chemistry, Bioorg.
Med. Chem. Lett. 1997, 7, 1903-1908.
254. P. G. Eis, J. A.
Smith, J. M. Rydzewski, D. A. Case, D. L. Boger, and W. J. Chazin, High
resolution solution structure of a DNA duplex alkylated by the antitumor
agent duocarmycin SA, J. Mol. Biol. 1997, 272,
237-252.
253. D. L.
Boger, N.-E. Haynes, M. S. Warren, J. Ramcharan, P. A. Kitos, and S. J.
Benkovic, A multisubstrate analog based on 5,8,10-trideazafolate, Bioorg.
Med. Chem. 1997, 5, 1853-1858.
252. D. L.
Boger, N.-E. Haynes, M. S. Warren, J. Ramcharan, A. E. Marolewski, P. A.
Kitos, and S. J. Benkovic, Abenzyl 10-formyl-trideazafolic acid (abenzyl
10-formyl-TDAF): an effective inhibitor of glycinamide ribonucleotide
transformylase, Bioorg. Med. Chem. 1997, 5,
1847-1852.
251. D. L.
Boger, N.-E. Haynes, M. S. Warren, J. Ramcharan, P. A. Kitos, and S. J.
Benkovic, Functionalized analogs of 5,8,10-trideazafolate: development
of an enzyme-assembled tight binding inhibitor of GAR Tfase and an
irreversible inhibitor of AICAR Tfase, Bioorg. Med. Chem. 1997,
5, 1839-1846.
250. D. L.
Boger, N.-E. Haynes, M. S. Warren, L. T. Gooljarsingh, J. Ramcharan, P.
A. Kitos, and S. J. Benkovic, Functionalized analogs of
5,8,10-trideazafolate as potential inhibitors of GAR Tfase or AICAR
Tfase, Bioorg. Med. Chem. 1997, 5,
1831-1838.
249. D. L.
Boger, N.-E. Haynes, P. A. Kitos, M. S. Warren, J. Ramcharan, A. E.
Marolewski, and S. J. Benkovic, 10-Formyl-5,8,10-trideazafolic acid
(10-formyl-TDAF): a potent inhibitor of glycinamide ribonucleotide
transformylase, Bioorg. Med. Chem. 1997, 5,
1817-1830.
248. D. L.
Boger, S. Teramoto, and H. Cai, N-Methyl-L-threonine analogs of
deglycobleomycin A2: synthesis and evaluation, Bioorg.
Med. Chem. 1997, 5, 1577-1590.
247. D. L. Boger, R. M.
Borzilleri, S. Nukui, and R. T. Beresis, Synthesis of the vancomycin CD
and DE ring systems, J. Org. Chem. 1997, 62,
4721-4736.
246. S. M.
Sakya, K. K.Groskopf, and D. L. Boger, Preparation and inverse electron
demand Diels-Alder reactions of
3-methoxy-6-methylthio-1,2,4,5-tetrazine, Tetrahedron Lett. 1997,
38, 3805-3808.
245. D. L. Boger, Applications of free radicals in organic synthesis, Israel
J. Chem. 1997, 37, 119-129.
(Commemorative issue honoring G. Stork and S. J. Danishefsky receipt of
the Wolf Prize in Chemistry).
244. D. L. Boger, B.
Bollinger, D. L. Hertzog, D. S. Johnson, H. Cai, P. Mésini, R. M.
Garbaccio, Q. Jin, and P. A. Kitos, Reversed and sandwiched analogs of
duocarmycin SA: establishment of the origin of the sequence selective
alkylation of DNA and new insights into the source of catalysis, J.
Am. Chem. Soc. 1997, 119, 4987-4998.
243. D. L. Boger, D. L.
Hertzog, B. Bollinger, D. S. Johnson, H. Cai, J. Goldberg, and P.
Turnbull, Duocarmycin SA shortened, simplified, and extended agents: a
systematic examination of the role of the DNA binding subunit, J.
Am. Chem. Soc. 1997, 119, 4977-4986.
242. D. L.
Boger and J.-H. Chen, An exceptionally potent analog of sandramycin, Bioorg.
Med. Chem. Lett. 1997, 7, 919-922.
241. D. L. Boger, C. W.
Boyce, R. M. Garbaccio, and J. A. Goldberg, CC-1065 and the
duocarmycins: synthetic studies, Chem. Rev. 1997,
97, 787-828.
240. D. L. Boger, J. Zhou,
R. M. Borzilleri, S. Nukui, and S. L. Castle, Synthesis of (9R,12S)-
and (9S,12S)-cycloisodityrosine and their N-methyl
derivatives J. Org. Chem. 1997, 62,
2054-2069.
239. D. L.
Boger, W. Chai, R. S. Ozer, and C.-M. Andersson, Solution-phase
combinatorial synthesis via the olefin metathesis reaction, Bioorg.
Med. Chem. Lett. 1997, 7, 463-468.
238. D. L. Boger, M.
Hikota, and B. M. Lewis, Determination of the relative and absolute
stereochemistry of fostriecin (CI-920), J. Org. Chem. 1997,
62, 1748-1753.
237. D. L.
Boger, C. W. Boyce, and D. S. Johnson, pH Dependence of the rate of DNA
alkylation for (+)-duocarmycin SA and (+)-CCBI-TMI, Bioorg. Med.
Chem. Lett. 1997, 7, 233-238.
236. D. L. Boger, J. A.
McKie, and C. W. Boyce, Asymmetric synthesis of the CBI alkylation
subunit of the CC-1065 and duocarmycin analogs, Synlett 1997,
515-517.
235. D. L. Boger, J. A.
McKie, T. Nishi, and T. Ogiku, Total synthesis of (+)-duocarmycin A, epi-(+)-duocarmycin
A and their unnatural enantiomers: assessment of chemical and biological
properties, J. Am. Chem. Soc. 1997, 119,
311-325.
234. D. L.
Boger and R. M. Garbaccio, Catalysis of the CC-1065 and duocarmycin DNA
alkylation reaction: DNA binding induced conformational change in the
agent results in activation, Bioorg. Med. Chem. 1997,
5, 263-276.
233. D. L.
Boger and N. Han, CC-1065/duocarmycin and bleomycin A2 hybrid
agents: lack of enhancement of DNA alkylation by attachment to
noncomplementary DNA binding subunits, Bioorg. Med. Chem. 1997,
5, 233-244.
232. B. F. Cravatt, D. K.
Giang, S. P. Mayfield, D. L. Boger, R. A. Lerner, and N. B. Gilula,
Molecular characterization of an enzyme that degrades neuromodulatory
fatty acid amides, Nature 1996, 384,
83-87.
231. D. L.
Boger, B. Bollinger, and D. S. Johnson, Examination of the role of the
duocarmycin SA methoxy substituents: identification of the minimum,
fully potent DNA binding subunit, Bioorg. Med. Chem. Lett. 1996,
6, 2207-2212.
230. D. L.
Boger, J. A. Goldberg, and J. A. McKie, A comparative study of the
solvolysis reactivity, regioselectivity, and stereochemistry of the
duocarmycin A and SA alkylation subunits, Bioorg. Med. Chem. Lett.
1996, 6, 1955-1960.
229. D. L. Boger and T. J.
Jenkins, Synthesis, X-ray structure, and properties of
fluorocyclopropane analogs of the duocarmycins incorporating the
9,9-difluoro-1,2,9,9a-tetrahydrocyclopropa-[c]benz[e]indol-4-one
(F2CBI) alkylation subunit, J. Am. Chem. Soc. 1996,
118, 8860-8870.
228. D. L.
Boger and J. Zhou, Key Analogs of the tetrapeptide subunit of RA-VII and
deoxybouvardin, Bioorg. Med. Chem. 1996, 4,
1597-1603.
227. C. M. Tarby, S. Cheng, and D. L. Boger, Solution phase strategy for
the synthesis of chemical libraries containing small organic molecules: a
general depeptide mimetic and a flexible universal template, in Molecular
Diversity and Combinatorial Chemistry: Libraries and Drug Discovery;
Chaiken, I. M.; Janda, K. D., Eds.; ACS: Washington; 1996, 81-98.
226. D. L. Boger, N. Han,
C. M. Tarby, C. W. Boyce, H. Cai, Q. Jin, and P. A. Kitos, Synthesis,
chemical properties, and preliminary evaluation of substituted CBI
analogs of CC-1065 and the duocarmycins incorporating the
7-cyano-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one
(CCBI) alkylation subunit: Hammett quantitation of the magnitude of
electronic effects on functional reactivity, J. Org. Chem. 1996,
61, 4894-4912.
225. J. E. Patterson, I.
R. Ollmann, B. F. Cravatt, Dale L. Boger, C.-H. Wong, and R. A. Lerner,
Inhibition of oleamide hydrolase catalyzed hydrolysis of the endogenous
sleep-inducing lipid: cis-9-octadecenamide, J. Am. Chem.
Soc. 1996, 118, 5938-5945.
224. D. L.
Boger, J. Zhou, R. M. Borzilleri, and S. Nukui, Synthesis of (9S,12S)-cycloisodityrosine
and its unnatural (9R,12S)-diastereomer, Bioorg.
Med. Chem. Lett. 1996, 6, 1089-1092.
223. D. L. Boger and J.
Zhou, An alternative synthesis of the cycloisodityrosine subunit of
deoxybouvardin and RA-VII and related agents: reassignment of the
stereochemistry of prior intermediates, J. Org. Chem. 1996,
61, 3938-3939.
222. D. L.
Boger, J. Zhou, and H. Cai, Demonstration and definition of the
noncovalent binding selectivity of agents related to CC-1065 by an
affinity cleavage agent: noncovalent binding coincidental with
alkylation, Bioorg. Med. Chem. 1996, 4,
859-868.
221. S.
Cheng, C. M. Tarby, D. D. Comer, J. P. Williams, L. H. Caporale, P. L.
Myers, and D. L. Boger, A solution-phase strategy for the synthesis of
combinatorial libraries containing small molecules: a universal and
dipeptidomimetic template, Bioorg. Med. Chem. 1996,
4, 727-737.
220. D. L. Boger, Cycloaddition reactions of azadienes, cyclopropenone
ketals and related systems: scope and applications, Chemtracts:
Organic Chem. 1996, 9, 149-189.
219. D. S. Johnson and D. L. Boger, DNA Binding Agents, Chapter 3 in Comprehensive
Supramolecular Chemistry, Vol. 4, J.-M. Lehn, Series Ed., Y.
Murakami, Vol. Ed., Pergamon Press, Oxford, England, 1996, 73-176.
218. D. L. Boger, Azadiene Diels-Alder reactions: scope and applications.
Total synthesis of natural and ent-fredericamycin A, J.
Heterocycl. Chem. 1996, 33, 1519-1531.
(review)
217. D. L. Boger and
D. S. Johnson, CC-1065 and the duocarmycins: understanding their
biological function through mechanistic studies, Angew. Chem., Int.
Ed. Engl. 1996, 35, 1438-1474.
216. D. L.
Boger, T. M. Ramsey, and H. Cai, Synthesis and Evaluation of potential Np
and Ns metal chelation sites
within the b-hydroxy-L-histidine subunit of
bleomycin A2: functional characterization of imidazole Np
metal complexation, Bioorg. Med. Chem. 1996,
4, 195-208.
215. D. L.
Boger, S. Teramoto, and H. Cai, Synthesis and evaluation
deglycobleomycin A2 analogs containing a tertiary N-methyl
amide and simple ester replacement for the L-histidine secondary amide:
direct functional characterization of the requirement for secondary
amide metal complexation, Bioorg. Med. Chem. 1996,
4, 179-194.
214. D. L. Boger, R. M.
Borzilleri, and S. Nukui, Synthesis of (R)-3,5-dihydroxy-4-methoxyphenylglycine
derivatives: the central amino acid of vancomycin and related agents, J.
Org. Chem. 1996, 61, 3561-3565.
213. D. L.
Boger, J. A. McKie, N. Han, C. M. Tarby, H. W. Riggs, and P. A. Kitos, A
Hammett correlation for CC-1065 and duocarmycin analogs: magnitude of
substituent electronic effects on functional reactivity Bioorg.
Med. Chem. Lett. 1996, 6, 659-664.
212. D. L. Boger, J. A.
McKie, H. Cai, B. Cacciari, and P. G. Baraldi, Synthesis and properties
of substituted CBI analogs of CC-1065 and the duocarmycins incorporating
the 7-methoxy-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one
(MCBI) alkylation subunit: magnitude of electronic effects on the
functional reactivity, J. Org. Chem. 1996, 61,
1710-1729.
211. S. Cheng, D. D.
Comer, J. P. Williams, P. L. Myers, and D. L. Boger, A novel
solution-phase strategy for the synthesis of chemical libraries
containing small organic molecules, J. Am. Chem. Soc. 1996,
118, 2567-2573.
210. D. L. Boger, J. A.
McKie, T. Nishi, and T. Ogiku, Enantioselective total synthesis of
(+)-duocarmycin A, epi-(+)-duocarmycin A and their unnatural
enantiomers, J. Am. Chem. Soc. 1996, 118,
2301-2302.
209. D. L. Boger, C. M.
Tarby, P. L. Myers, and L. H. Caporale, A generalized dipeptidomimetic
template: solution phase parallel synthesis of combinatorial libraries,
J. Am. Chem. Soc. 1996, 118,
2109-2110.
208. D. L. Boger, J.-H.
Chen, and Kurt W. Saionz, (-)-Sandramycin: total synthesis and
characterization of DNA binding properties, J. Am. Chem. Soc.
1996, 118, 1629-1644.
207. B. F. Cravatt, R. A.
Lerner, and D. L. Boger, Structure determination of an endogenous
sleep-inducing lipid, cis-9-octadecenoamide (oleamide): a
synthetic approach to the chemical analysis of trace quantities of a
natural product, J. Am. Chem. Soc. 1996, 118,
580-590.
206. D. L.
Boger, R. M. Borzilleri, and S. Nukui, Synthesis of appropriately
functionalized vancomycin CD and DE ring systems, Bioorg. Med.
Chem. Lett. 1995, 5, 3091-3096.
205. D.
L. Boger and K. Takahashi, Total synthesis of granditropone,
grandirubrine, imerubrine and isoimerubrine, J. Am. Chem. Soc.
1995, 117, 12452-12459.
204. D. L. Boger, O.
Hüter, K. Mbiya, and M. Zhang, Total synthesis of natural and ent-fredericamycin,
J. Am. Chem. Soc. 1995, 117,
11839-11849.
203. D. L. Boger and P.
Mesini, DNA alkylation properties of CC-1065 and duocarmycin analogs
incorporating the 2,3,10,10a-tetrahydrocyclopropa[d]benzo[f]quinol-5-one
(CBQ) alkylation subunit: identification of subtle structural features
that contribute to the regioselectivity of the adenine N3 alkylation
reaction, J. Am. Chem. Soc. 1995, 117,
11647-11655.
202. D. L.
Boger, J. Zhou, B. Winter, and P. A. Kitos, Key analogs of the
tetrapeptide subunit of RA-VII and deoxybouvardin, Bioorg. Med.
Chem. 1995, 3, 1579-1593.
201. D. L.
Boger, W. Yun, and N. Han, 1,2,9,9a-Tetrahydrocyclopropa[c]benz[e]indol-4-one
(CBI) analogs of CC-1065 and the duocarmycins: synthesis and evaluation,
Bioorg. Med. Chem. 1995, 3,
1429-1453.
200. D. L. Boger and
J.-H. Chen, A modified Friedlander condensation for the synthesis of
3-hydroxyquinoline-2-carboxylates, J. Org. Chem. 1995,
60, 7369-7371.
199. D. L.
Boger, S. L. Colletti, S. Teramoto, T. M. Ramsey, and J. Zhou, Synthesis
of key analogs of bleomycin A2 that permit a systematic
evaluation of the linker region: identification of an exceptionally
prominent role for the L-threonine substituent, Bioorg. Med. Chem.
1995, 3, 1281-1295.
198. D. L. Boger and J.
Zhou, N-Desmethyl derivatives of deoxybouvardin and RA-VII:
synthesis and evaluation, J. Am. Chem. Soc. 1995,
117, 7364-7378.
197. D. L. Boger, M. A.
Patane, and J. Zhou, Solution phase conformational studies of the cyclic
peptide RA-VII: lithium chloride perturbation of the conformational
equilibria, J. Am. Chem. Soc. 1995, 117,
7357-7363.
196. D. L. Boger, S.
Teramoto, and J. Zhou, Key synthetic analogs of bleomycin A2
that directly address the effect and role of the disaccharide:
demannosylbleomycin A2 and a-D-mannopyranosyldeglycobleomycin
A2, J. Am. Chem. Soc. 1995, 117,
7344-7356.
195. D. L. Boger, S.
Teramoto, T. Honda, and J. Zhou, synthesis and evaluation of the fully
functionalized bleomycin A2 metal binding domain containing
the 2-O-(3-O-carbamoyl-D-mannopyranosyl)-L-gulopyranosyl
disaccharide, J. Am. Chem. Soc. 1995, 117,
7338-7343.
194. D. L.
Boger and R. M. Borzilleri, An unusually facile SNAr 14-membered ring
biaryl ether macrocyclization reaction suitable for preparation of the
cycloisodityrosine subunit of bouvardin, deoxybouvardin and related
agents, Bioorg. Med. Chem. Lett. 1995, 5,
1187-1190.
193. B. F. Cravatt,
O. Prospero-Garcia, G. Szuidak, S. Henriksen, D. L. Boger, and R. A.
Lerner, Chemical characterization of a family of brain lipids that
induce sleep, Science 1995, 268,
1506-1509.
192. D. L. Boger and
D. S. Johnson, CC-1065 and the duocarmycins: unraveling the keys to a
new class of naturally derived DNA alkylating agents, Proc. Natl.
Acad. Sci. U.S.A. 1995, 92,
3642-3649.
191. D. L.
Boger, W. Yun, H. Cai, and N. Han, CBI-CDPBO1 and CBI-CDPBI1:
CC-1065 analogs containing deep-seated modifications in the DNA binding
subunits, Bioorg. Med. Chem. 1995, 3,
761-775.
190. D. L.
Boger, W. Yun, N. Han, and D. S. Johnson, CC-1065 CBI analogs: an
example of DNA alkylation efficiency enhancement through introduction of
stabilizing electrostatic interactions, Bioorg. Med. Chem. 1995,
3, 611-621.
189. D. L. Boger and J.
A. McKie, An efficient synthesis of 1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one
(CBI): an enhanced and simplified analog of the CC-1065 and duocarmycin
alkylation subunits, J. Org. Chem. 1995, 60,
1271-1275.
188. D. L. Boger and D.
S. Johnson, Second definitive test of proposed models for the origin of
the CC-1065 and duocarmycin DNA alkylation selectivity, J. Am.
Chem. Soc. 1995, 117, 1443-1444.
187. D. L. Boger, The
duocarmycins: synthetic and mechanistic studies, Acc. Chem. Res.
1995, 28, 20-29.
186. D. L.
Boger and T. Nishi, Diastereoselective Dieckmann condensation suitable
for introduction of the duocarmycin A C6 center: development of a
divergent strategy for the total synthesis of duocarmycins A and SA, Bioorg.
Med. Chem. 1995, 3, 67-77.
185. D. L. Boger, Total synthesis of (+)- and ent-(-)-duocarmycin
SA, in Advances in Nitrogen Heterocycles, Vol. 1, C. J. Moody,
Ed., JAI Press, 1995, 229-247.
184. D. L. Boger and P.
Mesini, Design, synthesis and evaluation of CC-1065 and duocarmycin
analogs incorporating the 2,3,10,10a-tetrahydro-1H-cyclopropa[d]benzo[f]quinol-5-one
(CBQ) alkylation subunit: identification and structural origin of subtle
stereoelectronic features that govern reactivity and regioselectivity, J.
Am. Chem. Soc. 1994, 116,
11335-11348.
183. D. L. Boger, M. A.
Patane, and J. Zhou, Total synthesis of bouvardin, O-methyl
bouvardin and O-methyl N9-desmethylbouvardin,
J. Am. Chem. Soc. 1994, 116,
8544-8556.
182. R. A. Lerner,
G. Siuzdak, O. Prospero-Garcia, S. J. Hendriksen, Dale L. Boger, and B.
F. Cravatt, Cerebrodiene: a brain lipid isolated from sleep-deprived
cats, Proc. Natl. Acad. Sci. U.S.A. 1994, 91,
9505-9508.
181. D. L. Boger, R. A.
Lerner, and B. F. Cravatt, Synthesis of a functionalized rigid
bicyclo[2.2.1]heptane: a useful hapten for eliciting catalytic
antibodies, J. Org. Chem. 1994, 59,
5078-5079.
180. D. L. Boger and M.
J. Kochanny, Inverse electron demand Diels-Alder reactions of
heterocyclic azadienes: [4 + 2] cycloaddition reactions of amidines with
1,3,5-triazines, J. Org. Chem. 1994, 59,
4950-4955.
179. D. L. Boger, T.
Nishi, and B. R. Teegarden, A p-quinonemethide analog of the
CC-1065 and duocarmycin alkylation subunits, J. Org. Chem. 1994,
59, 4943-4949.
178. D. L. Boger and Y.
Zhu, Diels-Alder reactions of cyclopropenone ketals: a concise tropolone
annulation applicable to rubrolone C ring introduction, J. Org.
Chem. 1994, 59, 3453-3458.
177. D. L. Boger and W.
Yun, CBI-TMI: synthesis and evaluation of a key analog of the
duocarmycins. Validation of a direct relationship between chemical
solvolytic stability and cytotoxic potency and confirmation of the
structural features responsible for the distinguishing behavior of
enantiomeric pairs of agents, J. Am. Chem. Soc. 1994,
116, 7996-8006.
176. D. L. Boger, P.
Mesini, and C. M. Tarby, Chemical and structural comparison of N-BOC-CBQ
and N-BOC-CBI: identification and structural origin of an
unappreciated but productive stability of the CC-1065 and duocarmycin SA
alkylation subunits, J. Am. Chem. Soc. 1994,
116, 6461-6462.
175. B. F. Cravatt, J.
A. Ashley, K. D. Janda, D. L. Boger, and R. A. Lerner, Crossing extreme
mechanistic barriers by antibody catalysis: syn elimination to a cis
olefin, J. Am. Chem. Soc. 1994, 116,
6013-6014.
174. D. L. Boger and T.
Honda, Total synthesis of bleomycin A2 and related agents. 4.
Synthesis of the disaccharide subunit: 2-O-(3-O-carbamoyl--D-mannopyranosyl)-L-gulopyranose
and completion of the total synthesis of bleomycin A2, J.
Am. Chem. Soc. 1994, 116, 5647-5656.
173. D. L. Boger, T.
Honda, R. F. Menezes, and S. L. Colletti, Total synthesis of bleomycin A2
and related agents. 3. Synthesis and comparative evaluation of
deglycobleomycin A2, epi-deglycobleomycin A2,
deglycobleomycin A1, desacetamido, descarboxamido, desmethyl
and desimidazole deglycobleomycin A2, J. Am. Chem. Soc.
1994, 116, 5631-5646.
172. D. L. Boger, T.
Honda, and Q. Dang, Total synthesis of bleomycin A2 and
related agents. 2. Synthesis of (-)-pyrimidoblamic acid, epi-(+)-pyrimidoblamic
acid, (+)-desacetamidopyrimidoblamic acid, and
(-)-descarboxamidopyrimidoblamic acid, J. Am. Chem. Soc. 1994,
116, 5619-5630.
171. D. L. Boger, S. L.
Colletti, T. Honda, and R. F. Menezes, Total synthesis of bleomycin A2
and related agents. 1. Synthesis and DNA binding properties of the
extended C-terminus: tripeptide S, tetrapeptide S, pentapeptide S, and
related agents, J. Am. Chem. Soc. 1994, 116,
5607-5618.
170. D. L. Boger and W.
Yun, Role of the CC-1065 and duocarmycin N2 substituent:
validation of a direct relationship between solvolysis chemical
stability and in vitro biological potency, J. Am. Chem.
Soc. 1994, 116, 5523-5524.
169. D. L. Boger, Design, synthesis, and evaluation of DNA minor groove
binding agents: the duocarmycins, Pure Appl. Chem. 1994,
66, 837-844.
168. F. Mohamadi, M. M.
Spees, G. S. Staten, P. Marder, J. K. Kipka, D. A. Johnson, D. L. Boger,
and H. Zarrinmayeh, Total synthesis and biological properties of novel
antineoplastic (chloromethyl)furanoindolines: an asymmetric
hydroboration mediated synthesis of the alkylation subunits, J.
Med. Chem. 1994, 37, 232-239.
167. W.
Wrasidlo, D. S. Johnson, and D. L. Boger, Induction of endonucleolytic
DNA fragmentation and apoptosis by the duocarmycins, Bioorg. Med.
Chem. Lett. 1994, 4, 631-636.
166. D. L.
Boger, D. S. Johnson, W. Yun, and C. M. Tarby, Molecular basis for
sequence selective DNA alkylation by (+)- and ent-(-)-CC-1065
and related agents: alkylation site models that accommodate the offset
AT-rich adenine N3 alkylation selectivity, Bioorg. Med. Chem.
1994, 2, 115-135.
165. D. L.
Boger, M. A. Patane, Q. Jin, and P. A. Kitos, Design, synthesis and
evaluation of bouvardin, deoxybouvardin and RA-I - XIV pharmacophore
analogs, Bioorg. Med. Chem. 1994, 2,
85-100.
164. D. L. Boger, D. S.
Johnson, and W. Yun, (+)- and ent-(-)-Duocarmycin SA and (+)-
and ent-(-)-N-BOC-DSA DNA alkylation properties.
Alkylation site models that accommodate the offset AT-rich adenine N3
alkylation selectivities of the enantiomeric agents, J. Am. Chem.
Soc. 1994, 116, 1635-1656.
163. D. L. Boger, T.
Honda, R. F. Menezes, S. L. Colletti, Q. Dang, and W. Yang, Total
synthesis of (+)-P-3A, epi-(-)-P-3A, and (-)-desacetamido
P-3A, J. Am. Chem. Soc. 1994, 116,
82-92.
162. D. L. Boger and
J.-H. Chen, (-)-Sandramycin: total synthesis and preliminary DNA binding
properties, J. Am. Chem. Soc. 1993, 115,
11624-11625.
161. D. L. Boger and J.
Zhou, Total synthesis of (+)-piperazinomycin, J. Am. Chem. Soc.
1993, 115, 11426-11433.
160. D. L. Boger and C.
M. Baldino, d,l- and meso-Isochrysohermidin: total
synthesis and interstrand DNA cross-linking, J. Am. Chem. Soc.
1993, 115, 11418-11425.
159. D. L. Boger, K. C.
Cassidy, and S. Nakahara, Total synthesis of streptonigrone, J. Am.
Chem. Soc. 1993, 115, 10733-10741.
158. D. L. Boger and W.
Yun, Reversibility of the duocarmycin A and SA DNA alkylation reaction,
J. Am. Chem. Soc. 1993, 115,
9872-9873.
157. D. L. Boger, K.
Machiya, D. L. Hertzog, P. A. Kitos, and D. Holmes, Total Synthesis and
preliminary evaluation of (+)- and ent-(-)-duocarmycin SA, J.
Am. Chem. Soc. 1993, 115, 9025-9036.
156. H. H. Wasserman, R.
W. DeSimone, D. L. Boger, and C. M. Baldino, Singlet oxygen oxidation of
bipyrroles: total synthesis of d,l- and meso-isochrysohermidin,
J. Am. Chem. Soc. 1993, 115,
8457-8458.
155. D. L. Boger and J.
Zhou, CDPI3-enediyne and CDPI3-EDTA conjugates: a
new class of DNA cleaving agents, J. Org. Chem. 1993,
58, 3018-3024.
154. D. L. Boger, D.
Yohannes, J. Zhou, and M. A. Patane, Total synthesis of
cycloisodityrosine, RA-VII, deoxybouvardin, and N29-desmethyl
RA-VII: identification of the pharmacophore and reversal of the subunit
functional roles, J. Am. Chem. Soc. 1993, 115,
3420-3430.
153. D. L. Boger and W.
L. Corbett, 4p participation of
1-aza-1,3-butadienes in [4 + 2] cycloaddition reactions: intramolecular
Diels-Alder reactions of a,b-unsaturated N-sulfonylimines,
J. Org. Chem. 1993, 58, 2068-2074.
152. D. L.
Boger and T. Honda, Studies on the synthesis of bleomycin A2
and P-3A: a diastereoselective imine addition reaction for C2-acetamido
side chain introduction, Tetrahedron Letters 1993,
34, 1567-1570.
151. D. L.
Boger, D. S. Johnson, M. S. S. Palanki, P. A. Kitos, J. Chang, and P.
Dowell, Evaluation of functional analogs of CC-1065 and the duocarmycins
incorporating the cross-linking
9a-chloromethyl-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one
(C2BI) alkylation subunit, Bioorg. Med. Chem. 1993,
1, 27-38.
150. D. L. Boger, Y.
Nomoto, and B. R. Teegarden, Vancomycin and ristocetin models: synthesis
via the Ullmann macrocyclization reaction, J. Org. Chem. 1993,
58, 1425-1433.
149. D. L. Boger, Design, synthesis and evaluation of DNA minor groove
binding agents, Pure Appl. Chem. 1993, 65,
1123-1132.
148. D. L. Boger, R.
F. Menezes, and T. Honda, Total synthesis of (-)-pyrimidoblamic acid and
deglycobleomycin A2, Angew. Chem., Int. Ed. Engl. 1993,
32, 273-275.
147. D. L.
Boger and D. Yohannes, K-13 and OF4949: evaluation of key partial
structures and pharmacophore delineation, Bioorg. Med. Chem. Lett.
1993, 3, 245-250.
146. D. L.
Boger and W. Yang, P-3A and (-)-desacetamido P-3A: demonstration and
study of their effective functional cleavage of duplex DNA, Bioorg.
Med. Chem. Lett. 1992, 2, 1649-1654.
145. D. L. Boger and K.
Machiya, Total synthesis of (+)-duocarmycin SA, J. Am. Chem. Soc.
1992, 114, 10056-10058.
144. D. L. Boger and M.
S. S. Palanki, Functional analogs of CC-1065 and the duocarmycins
incorporating the 9a-chloromethyl-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one
(C2BI) alkylation subunit: synthesis and preliminary DNA
alkylation studies, J. Am. Chem. Soc. 1992,
114, 9318-9327.
143. D. L.
Boger, R. F. Menezes, and W. Yang, A simple procedure for the
purification and isolation of bleomycin A2, Bioorg. Med.
Chem. Lett. 1992, 2, 959-962.
142. D. L. Boger and W.
L. Corbett, A convenient and general preparation of N-sulfonylimines,
J. Org. Chem. 1992, 57, 4777-4780.
141. D. L.
Boger, W. Yun, S. Terashima, Y. Fukuda, K. Nakatani, P. A. Kitos and Q.
Jin, DNA alkylation properties of the duocarmycins: (+)-duocarmycin A, epi-(+)-duocarmycin
A, ent-(-)-duocarmycin A, and epi,ent-(-)-duocarmycin
A, Bioorg. Med. Chem. Lett. 1992, 2,
759-765.
140. D. L. Boger, R. F.
Menezes, and Q. Dang, Synthesis of desacetamidopyrimidoblamic acid and
deglyco desacetamidobleomycin A2, J. Org. Chem. 1992,
57, 4333-4336.
Correction: J. Org.
Chem. 1992, 57, 5276.
139. D. L. Boger and R.
F. Menezes, Synthesis of tri- and tetrapeptide S: the extended
C-terminus of bleomycin A2, J. Org. Chem. 1992,
57, 4331-4333.
138. D. L. Boger and M.
Zhang, A concise synthesis of the fredericamycin A DEF ring system: [4 +
2] cycloaddition reactions of 1-aza-1,3-butadienes, J. Org. Chem.
1992, 57, 3974-3977.
137. D. L. Boger, W.
Yun, and B. R. Teegarden, An improved synthesis of
1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one
(CBI): a simplified analog of the CC-1065 alkylation subunit, J.
Org. Chem. 1992, 57, 2873-2876.
136. D. L. Boger and S.
A. Munk, DNA alkylation properties of CBI-based agents: enhanced
functional analogs of CC-1065 incorporating the
1,2,9,9a-tetrahydrocycloprop[1,2-c]benz[1,2-e]indol-4-one
(CBI) alkylation subunit, J. Am. Chem. Soc. 1992,
114, 5487-5496.
135. D. L.
Boger, R. F. Menezes, Q. Dang, and W. Yang, Deglyco
GABA,gly-desacetamidobleomycin A2: a simplified synthetic
model for bleomycin A2, Bioorg. Med. Chem. Lett. 1992,
2, 261-266.
134. D. L. Boger and T.
T. Curran, Synthesis of the lower subunit of rhizoxin, J. Org.
Chem. 1992, 57, 2235-2244.
133. D. L. Boger and Q.
Dang, Synthesis of desacetamido P-3A: 1,3,5-triazine-pyrimidine
heteroaromatic azadiene Diels-Alder reaction, J. Org. Chem. 1992,
57, 1631-1633.
132. D. L. Boger and R.
J. Mathvink, Acyl radicals: intermolecular and intramolecular alkene
addition reactions, J. Org. Chem. 1992, 57,
1429-1443.
131. D. L. Boger, D.
Yohannes, and J. B. Myers, Jr., Synthesis of N29-desmethyl
RA-VII. Identification of the pharmacophore of RA-I - RA-VII and
deoxybouvardin and reassignment of the subunit functional roles, J.
Org. Chem. 1992, 57, 1319-1321.
130. D. L. Boger and S.
M. Sakya, CC-1065 partial structures: enhancement of the noncovalent
affinity for DNA minor groove binding through introduction of
stabilizing electrostatic interactions, J. Org. Chem. 1992,
57, 1277-1284.
129. D. L. Boger, Design, synthesis, and evaluation of functional analogs
of (+)-CC-1065 and the duocarmycins, Proceedings of the 35th Robert
A. Welch Foundation Conference on Chemical Research, Chemistry at the
Frontiers of Medicine 1992, 35,
137-179.
128. D. L. Boger, Design, synthesis, and evaluation of functional analogs
of CC-1065 and the duocarmycins: a detailed study of factors effecting DNA
binding selectivity, in Advances in Heterocyclic Natural Products
Synthesis, Vol. 2, W. H. Pearson, ed., JAI Press, 1992, 1-188.
127. D. L.
Boger and Y. Zhu, Studies on the synthesis of rubrolone: 4p
participation of O-alkyl a,b-unsaturated
oximes in intramolecular [4 + 2] cycloaddition reactions, Tetrahedron
Letters 1991, 32, 7643-7646.
126. D. L. Boger, Duocarmycins: a new class of sequence selective DNA
minor groove alkylating agents, Chemtracts: Organic Chem. 1991,
4, 329-349.
125. D. L. Boger, [4 + 2] Cycloadditions: Heterodiene Additions, Chapter
4.3 in Comprehensive Organic Synthesis, Vol. 5, B. M. Trost and
I. Fleming, Series Ed.; L. Paquette, Vol. Ed., Pergamon Press, Oxford,
England, 1991, 451-512.
124. D. L. Boger and C.
M. Baldino, Singlet oxygen mediated oxidative decarboxylation of
pyrrole-2-carboxylic acids, J. Org. Chem. 1991,
56, 6942-6944.
123. D. L. Boger and J.
B. Myers, Jr., Design and synthesis of a conformational analog of
deoxybouvardin, J. Org. Chem. 1991, 56,
5385-5390.
122. D. L.
Boger, J. B. Myers, Jr., D. Yohannes, P. A. Kitos, O. Suntornwat, and J.
C. Kitos, Evaluation of bouvardin, deoxybouvardin, and RA-I - RA-VII
partial structures: reassignment of the pharmacophore, Bioorg. Med.
Chem. Lett. 1991, 1, 313-316.
121. D. L. Boger, J. S. Panek, and M. Patel, Preparation and inverse
electron demand Diels-Alder reaction of an electron-deficient heterocyclic
azadiene: dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate. 1,2-Diazine and
pyrrole introduction, Organic Syntheses 1991,
70, 79-92.
120. D. L. Boger, S. M.
Sakya, and D. Yohannes, Total synthesis of combretastatin D-2:
intramolecular Ullmann macrocyclization reaction, J. Org. Chem.
1991, 56, 4204-4207.
119. D. L. Boger, T.
Ishizaki, and H. Zarrinmayeh, Isolation and characterization of the
duocarmycin-adenine DNA adduct, J. Am. Chem. Soc. 1991,
113, 6645-6649.
118. D. L. Boger and M.
Zhang, Total synthesis of (±)-cis- and trans-trikentrin
A: Diels-Alder reactions of heteroaromatic azadienes, J. Am. Chem.
Soc. 1991, 113, 4230-4234.
117. D. L. Boger, S. A.
Munk, and H. Zarrinmayeh, The (+)-CC-1065 DNA alkylation: key studies
demonstrating a noncovalent binding selectivity contribution to the
alkylation selectivity, J. Am. Chem. Soc. 1991,
113, 3980-3983.
116. D. L. Boger, S. A.
Munk, and T. Ishizaki, The (+)-CC-1065 DNA alkylation: observation of an
unexpected relationship between cyclopropane electrophile reactivity and
the intensity of DNA alkylation, J. Am. Chem. Soc. 1991,
113, 2779-2780.
115. D. L. Boger and I.
C. Jacobson, Synthesis and preliminary evaluation of the fredericamycin
A ABCDE ring system, J. Org. Chem. 1991, 56,
2115-2122.
114. D. L.
Boger, T. Ishizaki, S. M. Sakya, S. A. Munk, P. A. Kitos, Q. Jin, and J.
M. Besterman, Synthesis and preliminary evaluation of (+)-CBI-indole2:
an enhanced functional analog of (+)-CC-1065, Bioorg. Med. Chem.
Lett. 1991, 1, 115-120.
113. D. L.
Boger, S. A. Munk, H. Zarrinmayeh, T. Ishizaki, J. Haught, and M. Bina,
An alternative and convenient strategy for generation of substantial
quantities of singly 5'-32P-end-labeled double-stranded DNA
for binding studies: development of a protocol for the examination of
the functional features of (+)-CC-1065 and the duocarmycins that
contribute to their sequence-selective DNA binding properties, Tetrahedron
1991, 47, 2661-2682.
112. D. L. Boger and D.
Yohannes, Intramolecular Ullmann condensation reaction: an effective
approach to macrocyclic diaryl ethers, J. Org. Chem. 1991,
56, 1763-1767.
111. D. L. Boger, W. L.
Corbett, T. T. Curran, and A. M. Kasper, Inverse electron demand
Diels-Alder reactions of N-sulfonyl a,b-unsaturated
imines: a general approach to the implementation of the 4p
participation of 1-aza-1,3-butadienes in Diels-Alder reactions, J.
Am. Chem. Soc. 1991, 113, 1713-1729.
110. D. L. Boger, H.
Zarrinmayeh, S. A. Munk, P. A. Kitos, and O. Suntornwat, Demonstration
of a pronounced effect of noncovalent binding selectivity on the
(+)-CC-1065 DNA alkylation and identification of the pharmacophore of
the alkylation subunit, Proc. Natl. Acad. Sci. U.S.A. 1991,
88, 1431-1435.
109. D. L. Boger and D.
Yohannes, Total synthesis of deoxybouvardin and RA-VII: macrocyclization
via an intramolecular Ullmann reaction, J. Am. Chem. Soc. 1991,
113, 1427-1429.
108. D. L. Boger, Design, synthesis, and evaluation of functional analogs
of CC-1065, in Heterocycles in Bio-organic Chemistry, Bergman,
J.; Van der Plas, H. C.; Simonyi, M., Eds.; Royal Society of Chemistry:
Cambridge, 1991, 103-129.
107. D. L. Boger and S.
Nakahara, Diels-Alder reactions of N-sulfonyl
1-aza-1,3-butadienes: development of a synthetic approach to the
streptonigrone C ring, J. Org. Chem. 1991, 56,
880-884.
106. D. L.
Boger, T. Ishizaki, H. Zarrinmayeh, P. A. Kitos, and O. Suntornwat, A
potent, simple derivative of an analog of the CC-1065 alkylation
subunit, Bioorg. Med. Chem. Lett. 1991, 1,
55-58.
105. D. L. Boger, T.
Ishizaki, H. Zarrinmayeh, S. A. Munk, P. A. Kitos, and O. Suntornwat,
Duocarmycin DNA alkylation properties and identification, synthesis and
evaluation of agents incorporating the pharmacophore of the duocarmycin
alkylation subunit: identification of the CC-1065/duocarmycin common
pharmacophore, J. Am. Chem. Soc. 1990, 112,
8961-8971.
104. D. L. Boger and D.
Yohannes, Total synthesis of L,L-Isodityrosine and isodityrosine-derived
agents: K-13, OF4949-III, and OF4949-IV, J. Org. Chem. 1990,
55, 6000-6017.
103. D. L. Boger, T.
Ishizaki, P. A. Kitos, and O. Suntornwat, Synthesis of N-(tert-butyloxycarbonyl)-CBI,
CBI, CBI-CDPI1, and CBI-CDPI2: enhanced functional
analogs incorporating the 1,2,9,9a-tetrahydrocycloprop[1,2-c]benz[1,2-e]indol-4-one
(CBI) left-hand subunit, J. Org. Chem. 1990,
55, 5823-5832.
Correction: J. Org.
Chem. 1991, 56, 2946.
102. D. L. Boger, Diels-Alder reactions of azadienes: scope and
application, Bull. Soc. Chim., Belg. 1990, 99,
599-615.
101. D. L. Boger and R.
J. Mathvink, Tandem free ring expansion and 5-exo-dig 5-hexynyl
radical cyclization: a useful approach to fused bicyclic carbocycles, J.
Org. Chem. 1990, 55, 5442-5444.
100. D. L. Boger and T.
T. Curran, Diels-Alder reactions of 1-aza-1,3-butadienes:
room-temperature endo-selective LUMOdiene-controlled [4 + 2]
cycloaddition reactions of N-sulfonyl
4-ethoxycarbonyl-1-aza-1,3-butadienes, J. Org. Chem. 1990,
55, 5439-5442.
99. D. L. Boger, T.
Ishizaki, H. Zarrinmayeh, P. A. Kitos, and O. Suntornwat, Synthesis and
preliminary evaluation of agents incorporating the pharmacophore of the
duocarmycin/pyrindamycin alkylation subunit: identification of the
CC-1065/duocarmycin common pharmacophore, J. Org. Chem. 1990,
55, 4499-4502.
98. D. L. Boger and C. E. Brotherton-Pleiss, Thermal reactions of
cyclopropenone ketals. Key mechanistic features, scope, and application of
the cycloaddition reactions of cyclopropenone ketals and -delocalized
singlet vinylcarbenes: three-carbon 1,1-/1,3-dipoles; in Advances in
Cycloaddition Chemistry, Vol. 2, D. P. Curran, Ed., JAI Press,
1990, 147-219.
97. D. L. Boger, R. J.
Wysocki, Jr., and T. Ishizaki, Synthesis of N-phenylsulfonyl-CI,
N-(tert-butyloxycarbonyl)-CI, CI-CDPI1, and
CI-CDPI2: CC-1065 functional analogs incorporating the parent
1,2,7,7a-tetrahydrocycloprop[1,2-c]indol-4-one (CI) left-hand
subunit, J. Am. Chem. Soc. 1990, 112,
5230-5240.
96. D. L. Boger, R. S.
Coleman, B. J. Invergo, S. M. Sakya, T. Ishizaki, S. A. Munk, H.
Zarrinmayeh, P. A. Kitos, and S. C. Thompson, Synthesis and evaluation
of aborted and extended CC-1065 functional analogs: (+)- and (-)-CPI-PDE1;
(+)- and (-)-CPI-CDPI1; and (±)-, (+)-, and (-)-CPI-CDPI3.
Preparation of key partial structures and definition of an additional
functional role of the CC-1065 central and right-hand subunits, J.
Am. Chem. Soc. 1990, 112, 4623-4632.
95. D. L. Boger and R.
J. Mathvink, Intramolecular acyl radical-alkene addition reactions:
macrocyclization reactions, J. Am. Chem. Soc. 1990,
112, 4008-4011.
94. D. L. Boger and R.
J. Mathvink, Tandem free radical alkene addition reactions of acyl
radicals, J. Am. Chem. Soc. 1990, 112,
4003-4008.
93. D. L. Boger, W. L.
Corbett, and J. Mark Wiggins, Room temperature, endo specific
1-aza-1,3-butadiene Diels-Alder reactions: acceleration of the LUMOdiene-controlled
[4 + 2] cycloaddition reactions through noncomplementary
azadiene substitution, J. Org. Chem. 1990, 55,
2999-3000.
92. D. L.
Boger and T. Ishizaki, Resolution of a CBI precursor and incorporation
into the synthesis of (+)- and (-)-CBI, (+)- and (-)-CBI-CDPI1,
(+)- and (-)-CBI-CDPI2: enhanced functional analogs of
(+)-CC-1065. A critical appraisal of the proposed relationship between
electrophile reactivity, DNA binding properties, and cytotoxic potency,
Tetrahedron Letters 1990, 31,
793-796.
91. D. L. Boger and I.
C. Jacobson, Studies on the total synthesis of fredericamycin A.
Preparation of key partial structures and development of an
intermolecular alkyne-chromium carbene complex benzannulation
cyclization approach to the ABCD(E) ring system, J. Org. Chem.
1990, 55, 1919-1928.
90. D. L. Boger and H.
Zarrinmayeh, Regiocontrolled nucleophilic addition to
selectively-activated p-quinonediimines: alternative
preparation of a key intermediate employed in the preparation of the
CC-1065 left-hand subunit, J. Org. Chem. 1990,
55, 1379-1390.
89. D. L.
Boger, R. S. Coleman, B. J. Invergo, H. Zarrinmayeh, P. A. Kitos, S. C.
Thompson, T. Leong, and L. W. McLaughlin, A demonstration of the
intrinsic importance of stabilizing hydrophobic binding and noncovalent
van der Waals contacts dominant in the noncovalent CC-1065:DNA binding,
Chem.-Biol. Interactions 1990, 73,
29-52.
88. D. L. Boger and D.
Yohannes, Design and total synthesis of a conformational analog of
bouvardin/deoxybouvardin, Synlett 1990,
33-36.
87. D. L.
Boger and D. Yohannes, Total synthesis of OF4949-III and OF4949-IV:
unusual effects of remote substituents on macrocyclization reaction
rates, Tetrahedron Letters 1989, 30,
5061-5064.
86. D. L. Boger, T.
Ishizaki, R. J. Wysocki, Jr., S. A. Munk, P. A. Kitos, and O.
Suntornwat, Total synthesis and evaluation of (±)-N-(tert-butyloxycarbonyl)-CBI,
(±)-CBI-CDPI1, and (±)-CBI-CDPI2: CC-1065
functional analogs incorporating the equivalent
1,2,9,9a-tetrahydrocycloprop[1,2-c]benz[1,2-e]indol-4-one
(CBI) left-hand subunit, J. Am. Chem. Soc. 1989,
111, 6461-6463.
85. D. L. Boger and M. Patel, Recent applications of the inverse electron
demand Diels-Alder reaction, in Progress in Heterocyclic Chemistry,
1989, Vol. 1, H. Suschitzky and E. F. V. Scriven, Ed., Pergamon
Press, 1989, 30-64.
84. D. L.
Boger and D. Yohannes, Synthesis of isodityrosine, Tetrahedron
Letters 1989, 30, 2053-2056.
83. D. L.
Boger and I. C. Jacobson, Studies on the total synthesis of
fredericamycin A: development of an intermolecular alkyne-chromium
carbene complex cyclization approach to the ABCDE ring system, Tetrahedron
Letters 1989, 30, 2037-2040.
82. D. L. Boger and D.
Yohannes, Total synthesis of K-13, J. Org. Chem. 1989,
54, 2498-2502.
81. D. L. Boger and R.
J. Mathvink, Phenylselenoesters as effective precursors of acyl radicals
for use in intermolecular addition reactions, J. Org. Chem. 1989,
54, 1777-1779.
80. D. L. Boger and R.
J. Wysocki, Jr., Total synthesis of (±)-N-benzenesulfonyl- and
(±)-N-(tert-butyloxycarbonyl)-CI, (±)-CI-CDPI1,
and (±)-CI-CDPI2: CC-1065 functional analogs incorporating
the parent 1,2,7,7a-tetrahydrocycloprop[1,2-c]indol-4-one (CI)
left-hand subunit, J. Org. Chem. 1989, 54,
1238-1240.
79. D. L. Boger and A.
M. Kasper, A general solution to implementing the 4p
participation of 1-aza-1,3-butadienes in Diels-Alder reactions: inverse
electron demand Diels-Alder reactions of a,b-unsaturated
N-phenylsulfonylimines, J. Am. Chem. Soc. 1989,
111, 1517-1519.
78. D. L. Boger and R.
J. Wysocki, Jr., A study of the scope of the [4 + 2] cycloaddition
reactions of unactivated 1,3-oxazin-6-ones, J. Org. Chem. 1989,
54, 714-718.
77. D. L. Boger and R. S. Coleman, Natural and synthetic antitumor
agents: synthetic studies on CC-1065 and functionally-related agents, in Studies
in Natural Products Chemistry, Vol. 3, A.-u.-Rahman, Ed., Elsevier
Science Publishers, 1989, 301-389.
76. D. L. Boger and K.
D. Robarge, A divergent, de novo synthesis of carbohydrates
based on an accelerated inverse electron demand Diels-Alder reaction of
1-oxa-1,3-butadienes, J. Org. Chem. 1988, 53,
5793-5796.
75. D. L. Boger, L. R.
Cerbone, and D. Yohannes, Oxidative coupling of methyl
6-hydroxyindole-2-carboxylate with primary amines: preparation of
2-substituted methyl pyrrolo[2,3-e]benzoxazole-5-carboxylates,
J. Org. Chem. 1988, 53, 5163-5168.
74. D. L. Boger and R.
S. Coleman, Total synthesis of (±)-N2-phenylsulfonyl
CPI, (±)-CC-1065, (+)-CC-1065, ent-(-)-CC-1065, and the
precise, functional agents: (±)-CPI-CDPI2, (+)-CPI-CDPI2,
and (-)-CPI-CDPI2, J. Am. Chem. Soc. 1988,
110, 4796-4807.
73. D. L.
Boger and Q. Dang, Inverse electron demand Diels-Alder reactions of
2,4,6-tris(ethoxycarbonyl)-1,3,5-triazine and 2,4,6-tris(methylthio)-1,3,5-triazine:
pyrimidine introduction, Tetrahedron 1988, 44,
3379-3390.
72. D. L. Boger and R.
J. Wysocki, Jr., Thermal cycloaddition reactions of p-delocalized
singlet vinylcarbenes: three-carbon 1,1-/1,3-dipoles. The thermal
three-carbon + two-carbon cycloaddition, J. Org. Chem. 1988,
53, 3408-3421.
71. D. L. Boger and R.
J. Mathvink, Acyl radicals: functionalized free radicals for
intramolecular cyclization reactions, J. Org. Chem. 1988,
53, 3377-3379.
70. D. L. Boger and K.
D. Robarge, Accelerated inverse electron demand Diels-Alder reactions of
1-oxa-1,3-butadienes: [4 + 2] cycloaddition reactions of a,b-unsaturated
-keto esters, J. Org. Chem. 1988, 53,
3373-3377.
69. D. L. Boger, Diels-Alder reactions of heterocyclic azadienes:
development of a strategy for the total synthesis of streptonigrin,
lavendamycin, and synthetic quinoline-5,8-quinones, Strategies and
Tactics in Organic Synthesis, Vol. 2, T. Lindberg, Ed., Academic
Press, 1988, 2-56.
68. D. L. Boger and S.
M. Sakya, Inverse electron demand Diels-Alder reactions of 3,6-bis(methylthio)-1,2,4,5-tetrazine:
1,2-diazine introduction and direct implementation of a divergent
1,2,4,5-tetrazine-1,2-diazine-benzene (indoline/indole) Diels-Alder
strategy, J. Org. Chem. 1988, 53,
1415-1423.
67. D. L. Boger and M.
Patel, Total synthesis of prodigiosin, prodigiosene, and
desmethoxyprodigiosin: Diels-Alder reactions of heterocyclic azadienes
and development of an effective palladium(II)-promoted 2,2'-bipyrrole
coupling procedure, J. Org. Chem. 1988, 53,
1405-1415.
66. D. L. Boger and R. S. Coleman, Total Synthesis of (+)-CC-1065 and
ent-(-)-CC-1065, J. Am. Chem. Soc. 1988, 110,
1321-1323.
65. D. L. Boger and R. S. Coleman, Total Synthesis of (+)- and
(-)-CPI-CDPI2: (+)-3bR,4aS- and (-)-3bS,4aR-deoxy
CC-1065, J. Org. Chem. 1988, 53,
695-698.
64. D. L. Boger and D. Yohannes, Studies on the total synthesis of
bouvardin and deoxybouvardin: cyclic hexapeptide cyclization studies and
preparation of key partial structures, J. Org. Chem. 1988,
53, 487-499.
63. D. L. Boger, J. S. Panek, and M. Yasuda, Preparation and Diels-Alder
reaction of a reactive, electron-deficient heterocyclic azadiene: triethyl
1,2,4-triazine-3,5,6-tricarboxylate, Organic Syntheses 1987,
66, 142-150.
62. D. L. Boger and D. Yohannes, Selectively protected L-Dopa
derivatives: application of the benzylic hydroperoxide rearrangement, J.
Org. Chem. 1987, 52, 5283-5286.
61. D. L. Boger, M. Yasuda, L. A. Mitscher, S. D. Drake, P. A. Kitos, and
S. C. Thompson, Streptonigrin and lavendamycin partial structures. Probes
for the minimum, potent pharmacophore and chemical mechanism of action of
streptonigrin, lavendamycin and synthetic quinoline-5,8-quinones, J.
Med. Chem. 1987, 30, 1918-1928.
60. D. L. Boger and M. Yasuda, Streptonigrin and lavendamycin partial
structures. Preparation of
7-amino-2-(2'-pyridyl)quinoline-5,8-quinone-6'-carboxylic acid: a probe
for the minimum, potent pharmacophore of the naturally occurring
antitumor-antibiotics, J. Heterocycl. Chem. 1987,
24, 1253-1260.
59. D. L. Boger and M. Patel, Indole N-carbonyl compounds:
preparation and coupling of indole-1-carboxylic acid anhydride, J.
Org. Chem. 1987, 52, 3934-3936.
58. D. L. Boger and M. Patel, Total synthesis of prodigiosin, Tetrahedron
Letters 1987, 28, 2499-2502.
57. D. L. Boger and M. Patel, Activation and use of pyrrole-1-carboxylic
acid in the preparation of pyrrole N-carbonyl compounds:
pyrrole-1-carboxylic acid anhydride, J. Org. Chem. 1987,
52, 2319-2323.
56. D. L. Boger and R. S. Coleman, Further observations on the Lewis
acid-catalyzed benzylic hydroperoxide rearrangement: use of a boron
trifluoride etherate-hydrogen peroxide preformed, aged reagent, Tetrahedron
Letters 1987, 28, 1027-1030.
55. D. L. Boger, R. S. Coleman, and B. J. Invergo, Studies on the total
synthesis of CC-1065: preparation of a synthetic, simplified 3-carbamoyl
1,2-dihydro[3,2-e]indole dimer/trimer/tetramer (CDPI
dimer/trimer/tetramer) and development of methodology for PDE-I dimer
methyl ester formation, J. Org. Chem. 1987, 52,
1521-1530.
54. D. L. Boger and R. S. Coleman, Diels-Alder reactions of heterocyclic
azadienes: total synthesis of PDE-I, PDE-II, and PDE-I dimer methyl ester,
J. Am. Chem. Soc. 1987, 109,
2717-2727.
53. D. L. Boger, C. E. Brotherton, and G. I. Georg, Preparation and
three-carbon + two-carbon cycloaddition of a cyclopropenone ketal:
cyclopropenone 1,3-propanediyl ketal, Organic Syntheses 1987,
65, 32-40.
52. D. L. Boger and M. D. Mullican, Preparation and inverse electron
demand Diels-Alder reaction of an electron-deficient diene: methyl
2-oxo-5,6,7,8-tetrahydro-2H-1-benzopyran-3-carboxylate, Organic
Syntheses 1987, 65, 98-107.
51. D. L. Boger and R. S. Coleman, The benzylic hydroperoxide
rearrangement: observations on the preparative scope of a convenient
alternative to the Baeyer-Villiger rearrangement, J. Org. Chem.
1986, 51, 5436-5439.
50. D. L. Boger and R. S. Coleman, Diels-Alder cycloaddition of
heterocyclic azadienes: total synthesis of PDE-II methyl ester, J.
Org. Chem. 1986, 51, 3250-3252.
49. D. L. Boger, Diels-Alder cycloaddition reactions of heterocyclic
azadienes: scope and applications, Chem. Rev. 1986,
86, 781-793.
48. D. L. Boger and C. E. Brotherton, Thermal reactions of cyclopropenone
ketals. Application of the cycloaddition reactions of p-delocalized
singlet vinylcarbenes: three-carbon 1,1-/1,3-dipoles. An alternative
preparation of deacetamidocolchicine: formal total synthesis of
colchicine, J. Am. Chem. Soc. 1986, 108,
6713-6719.
47. D. L. Boger and C. E. Brotherton, Thermal reactions of cyclopropenone
ketals. Key mechanistic features and scope of the cycloaddition reactions
of p-delocalized singlet vinylcarbenes:
three-carbon 1,1-/1,3-dipoles, J. Am. Chem. Soc. 1986,
108, 6695-6713.
46. D. L. Boger and C. E. Brotherton, Diels-Alder cycloadditions of
cyclopropenone ketals: dual participation in inverse electron demand (LUMOdiene-controlled)
and normal (HOMOdiene- controlled) Diels-Alder reactions.
Approaches to the preparation of tropones, Tetrahedron 1986,
42, 2777-2785.
45. D. L. Boger and M. Yasuda, An improved and divergent introduction of
the streptonigrin and lavendamycin quinoline-5,8-quinone AB ring systems,
Heterocycles 1986, 24, 1067-1073.
44. D. L. Boger and M. Patel, Diels-Alder cycloadditions of rigid
dienophiles: a probe for allylic axial substituent control of p-facial
selectivity in the Diels-Alder reaction, Tetrahedron Letters 1986,
27, 683-686.
43. D. L. Boger, J. S. Panek, S. R. Duff, and M. Yasuda, Total synthesis
of lavendamycin methyl ester, J. Org. Chem. 1985,
50, 5790-5795.
42. D. L. Boger, S. R. Duff, J. S. Panek, and M. Yasuda, Inverse electron
demand Diels-Alder reactions of heterocyclic azadienes. Studies on the
total synthesis of lavendamycin: investigative studies on the preparation
of the CDE b-carboline ring system and AB
quinoline-5,8-quinone ring system, J. Org. Chem. 1985,
50, 5782-5789.
41. D. L. Boger, J. S. Panek, R. S. Coleman, J. Sauer, and F. X. Huber, A
direct, convenient preparation of dimethyl
1,2,4,5-tetrazine-3,6-dicarboxylate, J. Org. Chem. 1985,
50, 5377-5379.
40. D. L. Boger, M. D. Mullican, L. A. Mitscher, S. Drake, and P. A.
Kitos, Antimicrobial and antitumor properties of
9,10-dihydrophenanthrenes, structure-activity studies on juncusol, J.
Med. Chem. 1985, 28, 1543-1547.
39. D.
L. Boger and J. S. Panek, Inverse electron demand Diels-Alder reactions
of heterocyclic azadienes: formal total synthesis of streptonigrin, J.
Am. Chem. Soc. 1985, 107, 5745-5754.
38. D. L. Boger and C. E. Brotherton, Thermal, four-carbon + three-carbon
cycloaddition reaction of cyclopropenone ketals. Total synthesis of
deacetamidocolchicine: formal total synthesis of colchicine, J. Org.
Chem. 1985, 50, 3425-3427.
37. D. L. Boger, M. Patel, and F. Takusagawa, Regioselectivity of the
intermolecular Diels-Alder reaction of acyl nitroso compounds (C-nitrosocarbonyl
compounds) and nitrosoformates (O-nitrosocarbonyl compounds).
Preparation of functionalized, cis-D6-1-octalones,
J. Org. Chem. 1985, 50, 1911-1916.
36. D. L. Boger, M. D. Mullican, M. R. Hellberg, and M. Patel,
Preparation of optically-active, functionalized cis-D6-1-octalones,
J. Org. Chem. 1985, 50, 1904-1910.
35. D. L. Boger, C. E. Brotherton, and G. I. Georg, Thermal, three-carbon
+ two-atom cycloaddition of cyclopropenone ketals with carbon-heteroatom
double bonds: preparation of butenolides, furans, and g-keto
esters, Tetrahedron Letters 1984, 25,
5615-5619.
34. D. L. Boger and C. E. Brotherton, Effective, thermal one-carbon +
two-atom cycloaddition of cyclopropenone ketals with electron-deficient
olefins: cyclopropane formation, Tetrahedron Letters 1984,
25, 5611-5614.
33. D. L. Boger, R. S. Coleman, J. S. Panek and D. Yohannes, Thermal
cycloaddition of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate with
electron-rich olefins: 1,2-diazine, pyrrole introduction. Preparation of
octamethylporphin (OMP), J. Org. Chem. 1984, 49,
4405-4409.
32. D. L. Boger and M. Patel, Regioselectivity of the intermolecular
Diels-Alder reaction of acyl nitroso compounds (C-nitrosocarbonyl
compounds) and nitrosoformates (O-nitrosocarbonyl compounds), J.
Org. Chem. 1984, 49, 4098-4099.
31. D. L. Boger and J. S. Panek, Palladium(0)-mediated b-carboline
synthesis: preparation of the CDE ring system of lavendamycin, Tetrahedron
Letters 1984, 25, 3175-3178.
30. D. L. Boger, C. E. Brotherton, J. S. Panek, and D. Yohannes, Direct
introduction of nitriles via use of unstable Reissert intermediates:
convenient procedures for the preparation of 2-cyanoquinolines and
1-cyanoisoquinolines, J. Org. Chem. 1984, 49,
4056-4058.
29. D. L. Boger and C. E. Brotherton, Total synthesis of azafluoranthene
alkaloids: rufescine and imelutine, J. Org. Chem. 1984,
49, 4050-4055.
28. D. L. Boger and M. D. Mullican, Regiospecific total synthesis of
juncusol, J. Org. Chem. 1984, 49,
4045-4049.
27. D. L. Boger and M. D. Mullican, Inverse electron demand Diels-Alder
reactions of 3-carbomethoxy-2-pyrones. Controlled introduction of
oxygenated aromatics: benzene, phenol, catechol, resorcinol, pyrogallol
annulation. Regiospecific, total synthesis of sendaverine and a
preparation of 6,7-benzomorphans, J. Org. Chem. 1984,
49, 4033-4044.
26. D. L. Boger and R. S. Coleman, Intramolecular Diels-Alder reactions
of 1,2-diazines: general indoline synthesis. Studies on the preparation of
the central and right-hand segment of CC-1065, J. Org. Chem. 1984,
49, 2240-2245.
25. D. L. Boger and C. E. Brotherton, Effective, thermal three-carbon +
two-carbon cycloaddition for cyclopentenone formation: formal 1,3-dipolar
cycloaddition of cyclopropenone ketals, J. Am. Chem. Soc. 1984,
106, 805-807.
24. D. L. Boger and M. D. Mullican, Inverse electron demand Diels-Alder
reactions of 3-carbomethoxy-2-pyrones. Controlled introduction of
oxygenated aromatics: benzene, phenol, catechol, resorcinol, and
pyrogallol annulation, Tetrahedron Letters 1983,
24, 4939-4942.
23. D. L. Boger and J. S. Panek, 1,2,4-Triazine preparation via thermal
cycloaddition of 3,6-dicarbomethoxy-1,2,4,5-tetrazine with aryl
thioimidates, Tetrahedron Letters 1983, 24,
4511-4514.
22. D. L. Boger, Diels-Alder reactions of azadienes, Tetrahedron
1983, 39, 2869-2939. Tetrahedron Report No.
153.
21. D. L. Boger and J. S. Panek, Formal total synthesis of streptonigrin,
J. Org. Chem. 1983, 48, 621-623.
20. D. L. Boger and J. S. Panek, Pyridine construction via thermal
cycloaddition of 1,2,4-triazines with enamines: studies on the preparation
of the biaryl CD ring system of streptonigrin, J. Org. Chem. 1982,
47, 3763-3765.
19. D. L. Boger, M. D. Mullican, and M. Patel, Synthetic analgesics:
preparation of 6,7-benzomorphans, Tetrahedron Letters 1982,
23, 4559-4562.
18. D. L. Boger and M. D. Mullican, Regiospecific total synthesis of
juncusol, Tetrahedron Letters 1982, 23,
4555-4558.
17. D. L. Boger and M. D. Mullican, Inverse electron demand Diels-Alder
reaction of 3-carbomethoxy-2-pyrones with 1,1-dimethoxyethylene: a mild
method of aryl introduction, Tetrahedron Letters 1982,
23, 4551-4554.
16. D. L. Boger, J. Schumacher, J. S. Panek, M. D. Mullican, and M.
Patel, Thermal cycloaddition reaction of 1,3,5-triazine with enamines:
regiospecific pyrimidine annulation, J. Org. Chem. 1982,
47, 2673-2675.
15. D. L. Boger, J. S. Panek, and M. M. Meier, Diels-Alder reaction of
heterocyclic azadienes, 2. Catalytic Diels-Alder reactions of in situ
generated enamines with 1,2,4-triazines: general pyridine annulation, J.
Org. Chem. 1982, 47, 895-897.
14. D. L. Boger, C. E. Brotherton, and M. D. Kelley, A simplified
isoquinoline synthesis, Tetrahedron 1981, 37,
3977-3980.
13. D. L. Boger and C. E. Brotherton, Preparation of
3-vinyl-4-methyl-1,2,5-oxadiazole and 3-vinyl-4-methyl-1,2,5-thiadiazole,
J. Heterocyclic Chem. 1981, 18,
1247-1249.
12. D. L. Boger and J. S. Panek, Diels-Alder reaction of heterocyclic
azadienes, I. Thermal cycloaddition of 1,2,4-triazine with enamines: a
simple preparation of substituted pyridines, J. Org. Chem. 1981,
46, 2179-2182.
11. D. L. Boger and J. S. Panek, Preparation of (R)- and (S)-4-iodo-1,2-epoxybutane,
(R)- and (S)-(2-iodoethyl)oxirane, useful chiral
synthons, J. Org. Chem. 1981, 46,
1208-1210.
10. D. L. Boger and M. D. Mullican, A simple and convenient phenol
annulation, J. Org. Chem. 1980, 45,
5002-5004.
9. D. L. Boger, Part I: New annulation processes, Part II: Studies
directed toward a biomimetic synthetic approach to prostaglandins, Ph.D.
dissertation, Harvard University, February 1980, 238 pp.
8. D. L. Boger, A convenient preparation of 2-substituted benzothiazoles,
J. Org. Chem. 1978, 43, 2296-2297.
7. E. J. Corey and D. L. Boger, A new and unusually flexible scheme for
annulation to form fused cyclohexanone units, Tetrahedron Letters
1978, 4597-4600.
6. E. J. Corey and D. L. Boger, Oxidative cationic cyclization reactions
effected by pyridinium chlorochromate, Tetrahedron Letters 1978,
2461-2464.
5. D.
L. Boger, Concerning the stereochemistry of 9-methyl-D1-3-octalone,
Tetrahedron Letters 1978, 17-18.
4. E.
J. Corey and D. L. Boger, New annulation processes for fused and spiro
rings based on the chemistry of benzothiazoles, Tetrahedron Letters
1978, 13-16.
3. E.
J. Corey and D. L. Boger, Application of benzothiazoles to carbon-carbon
bond formation in organic synthesis, Tetrahedron Letters 1978,
9-13.
2. E.
J. Corey and D. L. Boger, Benzothiazoles as carbonyl equivalents, Tetrahedron
Letters 1978, 5-8.
1. A.
W. Burgstahler, D. L. Boger and N. K. Naik, Synthesis and chiroptical
properties of some asymmetric planar cisoid dienes, Tetrahedron
1976, 32, 309-315.
Books
Hetero Diels-Alder Methodology in Organic Synthesis, D. L. Boger and S.
M. Weinreb, Academic Press: San Diego, 1987.
Modern Organic Synthesis: Lecture Notes, Dale L. Boger, TSRI Press: San
Diego, 1999.
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