Selected Publications

The Boger Group, Key Reviews

Azadiene Diels-Alder Reactions: Scope and Applications

D. L. Boger, Diels-Alder reactions of azadienes, Tetrahedron 1983, 39, 2869-2939. Tetrahedron Report No.153.
D. L. Boger, Diels-Alder cycloaddition reactions of heterocyclic azadienes: scope and applications, Chem. Rev. 1986, 86, 781-793.
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.
D. L. Boger, Diels-Alder reactions of azadienes: scope and application, Bull. Soc. Chim., Belg. 1990, 99, 599-615.
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.
D. L. Boger, Cycloaddition reactions of azadienes, cyclopropenone ketals and related systems: scope and applications, Chemtracts: Organic Chem. 1996, 9, 149-189.
Book: Hetero Diels-Alder Methodology in Organic Synthesis, D. L. Boger and S. M. Weinreb, Academic Press: San Diego, 1987.

Cyclopropenone Ketal Cycloaddition Reactions: Scope and Applications

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 p-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.
D. L. Boger, Cycloaddition reactions of azadienes, cyclopropenone ketals and related systems: scope and applications, Chemtracts: Organic Chem. 1996, 9, 149-189.

Acyl Radicals and Related Free Radical Cyclizations

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).

CC-1065 and the Duocarmycins

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.
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.
D. L. Boger, Duocarmycins: a new class of sequence selective DNA minor groove alkylating agents, Chemtracts: Organic Chem. 1991, 4, 329-349.
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.
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.
D. L. Boger, The duocarmycins: synthetic and mechanistic studies, Acc. Chem. Res. 1995, 28, 20-29.
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.
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, 1439-1474.
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.
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.
M. S. Tichenor and D. L. Boger, Yatakemycin: Total synthesis, DNA Alkylation, and biological properties, Nat. Prod. Rep. 2008, 25, 220-226.
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.

Bleomycin A₂

D. L. Boger and H. Cai, Bleomycin: synthetic and mechanistic studies, Angew. Chem. Int. Ed. 1999, 38, 448-476.

DNA Binding Agents

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.
S. E. Wolkenberg and D. L. Boger, Mechanisms of in situ activation of DNA targeting antitumor agents, Chem. Rev. 2002, 102, 2477-2496.
W. C. Tse and D. L. Boger, Sequence-selective DNA recognition: natural products and nature’s lessons, Chem. Biol. 2004, 11, 1607-1617.
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.

Oleamide: An Endogenous Sleep-inducing Lipid and Prototypical Member of a New Class of Biological Signaling Molecules

D. L. Boger, S. J. Hendriksen, and B. F. Cravatt, Oleamide: An endogenous sleep-inducing lipid and prototypical member of a new class of biological signaling molecules, Current Pharm. Design 1998, 4, 303-314.
C. Ezzili, K. Otrubova, and D. L. Boger, Fatty acid amide signaling molecules, Bioorg. Med. Chem. Lett. 2010, 20, 5959-5968.(Invited BMCL Digest).

Combinatorial Chemistry

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.
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.
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.
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.
L. R. Whitby and D. L. Boger, Comprehensive peptidomimetic libraries targeting protein-protein interactions, Acc. Chem. Res. 2012, 45, 1698-1704.

Signal Transduction

D. L. Boger and J. Goldberg, Cytokine receptor dimerization and activation: prospects for small molecule agonists, Bioorg. Med. Chem. 2001, 9, 119-124.
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.
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.

Fostriecin

D. L. Boger, D. Lewy, and C.-M. Gauss, Fostriecin: chemistry and biology, Curr. Med. Chem. 2002, 9, 2005-2032.

Vancomycin, Teicoplanin, and Ramoplanin

D. L. Boger, Vancomycin, Teicoplanin, and Ramoplanin: Synthetic and Mechanistic Studies, Med. Chem. Rev. 2001, 21, 356-381. Keynote address at 4th Steamboat Springs Conference on Medicinal and Bioorganic Chemistry.
S. Walker, J. Helm, Y. Hu, L. Chen, Y. Rew, and D. L. Boger, Chemistry and biology of ramoplanin: a lipoglycodepsipeptide with potent antibiotic activity, Chem. Rev. 2005, 105, 449-476.
R. C. James, J. G. Piecrce, A. Okano, J. Xie, and D. L. Boger, Redesign of glycopeptide antiobiotics: back to the future, ACS Chem. Biol. 2012, 45, 1698-1704.

Chlorofusin
R. C. Clark, S. Y. Lee, M. Searcey, and D. L. Boger, Isolation, total synthesis, and structure elucidation of chlorofusin, a natural product inhibitor of the p53-MDM2 protein-protein interaction Nat. Prod. Rep. 2009, 105, 465-477.

FAAH Inhibitors

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)
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).

Natural Products Total Syntheses:

Sendaverine (M. D. Mullican), J. Org. Chem. 1984, 49, 4033-4044.
Juncusol (M. D. Mullican), J. Org. Chem. 1984, 49, 4045-4049.
Rufescine and Imelutine (C. E. Brotherton), J. Org. Chem. 1984, 49, 4050-4055.
Streptonigrin (J. S. Panek), J. Am. Chem. Soc. 1985, 107, 5745-5754.
Lavendamycin (J. S. Panek, S. R. Duff, M. Yasuda), J. Org. Chem. 1985, 50, 5782-5789, 5790-5795.
Colchicine (C. E. Brotherton), J. Am. Chem. Soc. 1986, 108, 6713-6719.
PDE-I and PDE-II (R. S. Coleman), J. Am. Chem. Soc. 1987, 109, 2717-2727.
(+)- and ent-(-)-CC-1065 (R. S. Coleman), J. Am. Chem. Soc. 1988, 110, 1321-1323, 4796-4807.
Prodigiosin and Prodigiosene (M. Patel), J. Org. Chem. 1988, 53, 1405-1415.
K-13 (D. Yohannes), J. Org. Chem. 1989, 54, 2498-2502.
OF4949-III and OF4949-IV (D. Yohannes), J. Org. Chem. 1990, 55, 6000-6017.
Deoxybouvardin and RA-VII (D. Yohannes), J. Am. Chem. Soc. 1991, 113, 1427-1429.
cis- and trans-Trikentrin A (M. Zhang), J. Am. Chem. Soc. 1991, 113, 4230-4234.
Combretastatin D-2 (S. Sakya, D. Yohannes), J. Org. Chem. 1991, 56, 4204-4207.
(+)- and ent-(-)-Duocarmycin SA (K. Machiya), J. Am. Chem. Soc. 1992, 114, 10056-10058.
d,l- and meso-Isochrysohermidin (C. M. Baldino), J. Am. Chem. Soc. 1993, 115, 11418-11425.
Streptonigrone (K. C. Cassidy, S. Nakahara), J. Am. Chem. Soc. 1993, 115, 10733-10741.
(+)-Piperazinomycin (J. Zhou), J. Am. Chem. Soc. 1993, 115, 11426-11433.
(-)-Sandramycin (J.-H. Chen), J. Am. Chem. Soc. 1993, 115, 11624-11625; 1996, 118, 1629-1644.
(+)-P-3A (T. Honda, S. L. Colletti, Q. Dang), J. Am. Chem. Soc. 1994, 116, 82-92.
Deglycobleomycin A₂ (T. Honda, R. F. Menezes, S. L. Colletti), J. Am. Chem. Soc. 1994, 116, 5631-5646.
Bleomycin A₂ (T. Honda), J. Am. Chem. Soc. 1994, 116, 5647-5656.
Bouvardin and O-Methyl Bouvardin (M. A. Patane, J. Zhou), J. Am. Chem. Soc. 1994, 116, 8544-8556.
Natural and ent-Fredericamycin A (O. Hueter, K. Mbiya, M. Zhang), J. Am. Chem. Soc. 1995, 117, 11839-11849.
Granditropone, Grandirubrine, Imerubrine, and Isoimerubrine (K. Takahashi), J. Am. Chem. Soc. 1995, 117, 12452-12459.
Oleamide (B. F. Cravatt), J. Am. Chem. Soc. 1996, 118, 580-590.
(+)- and ent-(-)-Duocarmycin A (J. A. McKie, T. Nishi, T. Ogiku), J. Am. Chem. Soc. 1996, 118, 2301-2302; 1997, 119, 311-325.
Nothapodytine and (-)-Mappicine (J. Hong), J. Am. Chem. Soc. 1998, 120, 1218-1222.
Ningalin A (C. W. Boyce), J. Am. Chem. Soc. 1999, 121, 54-62.
Lamellarin O and Lukianol A (M. A. Labroli), J. Am. Chem. Soc. 1999, 121, 54-62.
Permethyl Storniamide A (C. A. Sehon), J. Am. Chem. Soc. 1999, 121, 54-62.
Luzopeptins A-C (M. W. Ledeboer, M. Kume), J. Am. Chem. Soc. 1999, 121, 1098-1099; 11375-11383.
Phomazarin (J. Hong, M. Hikota, M. Ishida), J. Am. Chem. Soc. 1999, 121, 2471-2477.
Vancomycin Aglycon (S. Miyazaki, S. H. Kim, J. H. Wu, O. Loiseleur, S. L. Castle), J. Am. Chem. Soc. 1999, 121, 3226-3227; 10004-10011.
HUN-7293 (H. Keim), J. Am. Chem. Soc. 1999, 121, 6197-6205.
Quinoxapeptins A-C (M. W. Ledeboer, M. Kume), J. Am. Chem. Soc. 1999, 121, 11375-11383.
Ningalin B (D. Soenen), J. Org. Chem. 2000, 65, 2479-2483.
Distamycin A (B. Fink), J. Am. Chem. Soc. 2000, 122, 6382-6394.
Azatriostin A (J. K. Lee), J. Org. Chem. 2000, 65, 5996-6000.
Thiocoraline and BE-22179 (S. Ichikawa), J. Am. Chem. Soc. 2000, 122, 2956-2957; 2001, 123, 561-568.
Teicoplanin Aglycon (S. H. Kim, Y. Mori, J.-H. Weng, S. Miyazaki, H. Strittmatter, J. J. McAtee, O. Rogel, S. L. Castle), J. Am. Chem. Soc. 2000, 122, 7416-7417; 2001, 123, 1862-1871.
Rubrolone Aglycon (S. Ichikawa, H. Jiang), J. Am. Chem. Soc. 2000, 122, 12169-12173.
Hippadine, Anhydrolycorinium Chloride, Anhydrolycorinone (S. Wolkenberg), J. Org. Chem. 2000, 65, 9120-9124.
Fostriecin (S. Ichikawa, W. Zhong), J. Am. Chem. Soc. 2001, 123, 4161-4167.
(-)-Roseophilin (J. Hong), J. Am. Chem. Soc. 2001, 123, 8515-8519.
Ramoplanin A2 and Ramoplanose Aglycon (W. Jiang, J. Wanner, R. J. Lee, P.-Y. Bounaud), J. Am. Chem. Soc. 2002, 124, 5288-5290; 2003, 125, 1877-1887.
HUN-7293B (Y. Chen), J. Am. Chem. Soc. 2002, 124, 5431-5440.
(+)-Camptothecin (B. Blagg), Tetrahedron 2002, 58, 6343-6349.
Anhydrolycorinone (S. Wolkenberg), J. Org. Chem. 2002, 67, 7361-7364.
Ristocetin A Aglycon (B. Crowley, Y. Mori, C. McComas, D. Tang), J. Am. Chem. Soc. 2004, 126, 4310-4317.
(+)- and ent-(–)-Yatakemycin (M. Tichenor, D. Kastrinsky), J. Am. Chem. Soc. 2004, 126, 8396-8398.
Ramoplanin A1 and A3 Aglycons (Y. Rew, D. Shin), Proc. Natl. Acad. Sci. USA, 2004, 101, 11977-11979.
Natural and ent-Minovine (Z. Yuan, H. Ishikawa), Org. Lett. 2005, 7, 741-745.
Ningalin D (A. Hamasaki, J. Zimpleman), J. Am. Chem. Soc. 2005, 127, 10767-10770.
(–)- and ent-(+)-Vindoline (H. Ishikawa, Y. Choi, J. Velcicky, G. Elliott, M. Miller), Org. Lett. 2005, 7, 4539-4542; J. Am. Chem. Soc. 2006, 128, 10596-10612.
N-Methylaspidospermidine (H. Ishikawa), J. Am. Chem. Soc. 2006, 128, 10596-10612.
Piericidin A1 and B1 (M. Schnermann), J. Am. Chem. Soc. 2005, 127, 15704-15705; 2006, 128, 11799-11807.
(–)- and ent-(+)-Vindorosine (G. Elliott, J. Velcicky, H. Ishikawa), Angew. Chem. Int. Ed. 2006, 45, 620-622.
[Ψ(CH₂NH)Tpg⁴]Vancomycin Aglycon (B. M. Crowley), J. Am. Chem. Soc. 2006, 128, 2885-2892.
(+)- and ent-(–)-Yatakemycin, (+)- and ent-(–)-Duocarmycin SA (2nd generation, M. Tichenor), J. Am. Chem. Soc. 2006, 129, 15683-15696.
Cytostatin (B. Lawhorn, S. B. Boga), J. Am. Chem. Soc. 2006, 129, 16720-16732.
Ala scan of Ramoplanin (J. Nam, Y. Rew, D. Shin), J. Am. Chem. Soc. 2007, 129, 8747-8755.
Chlorofusin (S. Y. Lee, R. C. Clark), J. Am. Chem. Soc. 2007, 129, 9860-9861, 2008, 130, 12355-12369.
(+)- and ent-(-)-Vinblastine (H. Ishikawa, D. A. Colby), J. Am. Chem. Soc. 2008, 130, 420-421.
Iso-Duocarmycin SA and iso-yatakemycin (K. S. MacMillan), J. Am. Chem. Soc. 2009, 131, 1187-1194.
Vinblastine, vincristine, and related natural products (H. Ishikawa, D. Colby, S. Seto), J. Am. Chem. Soc. 2009, 131, 4904-4916.
Lycogarubin C and lycogalic acid (J. S. Oakdale) Org. Lett. 2010, 12, 1132-1134.
Chloropeptins (complestatin) (J. Garfunkle, H. Shimamura, F. S. Kimball, S. Breazanno) J. Am. Chem. Soc. 2009, 131, 16036-16038. 2010, 132, 7776-7783.
Phostriecin (aka sultriecin) (C. P. Burke), J. Am. Chem. Soc. 2010, 132, 2157-2159.
Fendleridine (aspidoalbidine) (E. L. Campbell, A. Zuhl), J. Am. Chem. Soc. 2010, 132, 3009-3012.
Vindoline and vindorosine (D. Kato, Y. Sasaki), J. Am. Chem. Soc. 2010, 132, 3685-3687 and 13533-13544.
Compleastatin A and B (S. P. Breazzano) J. Am. Chem. Soc. 2011, 133, 18495-18502.
[Ψ(C(=NH)]Tpg⁴]Vancomycin Aglycon (A. Okano, J. Xie, J. G. Pierce, R. C. James) J. Am. Chem. Soc. 2012, 134, 1284-1297.
(–)-Aspidospermine and (+)-Spegazzinine (J. P. Lajines, W. Jiang) Org. Lett. 2012, 14, 2078-2081.
Kopsinine (J. Xie, A. L. Wolfe), Org. Lett. 2013, 15, 868-870.

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