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Key Reviews and Natural Product Total Syntheses


Azadiene Diels-Alder Reactions: Scope and Applications

  • D. L. Boger, Diels-Alder reactions of azadienes, Tetrahedron 198339, 2869-2939. Tetrahedron Report No.153.
  • D. L. Boger, Diels-Alder cycloaddition reactions of heterocyclic azadienes: scope and applications, Chem. Rev. 198686, 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. 199099, 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. 19969, 149-189.
  • Book: Hetero Diels-Alder Methodology in Organic Synthesis, D. L. Boger and S. M. Weinreb, Academic Press: San Diego, 1987.
  • J. E. Sears and D. L. Boger, Tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition cascade of 1,3,4-oxadiazoles: initial scope and applications, Acc. Chem. Res. 2016, 49, 241-251.

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. 19969, 149-189.
Acyl Radicals and Related Free Radical Cyclizations

  • D. L. Boger, Applications of free radicals in organic synthesis, Israel J. Chem. 199737, 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. 19914, 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 199235, 137-179.
  • D. L. Boger, The duocarmycins: synthetic and mechanistic studies, Acc. Chem. Res. 199528, 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. 199592, 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. 199635, 1439-1474.
  • D. L. Boger, C. W. Boyce, R. M. Garbaccio, and J. A. Goldberg, CC-1065 and the duocarmycins: synthetic studies, Chem. Rev. 199797, 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. 199932, 1043-1052.
  • M. S. Tichenor and D. L. Boger, Yatakemycin: Total synthesis, DNA Alkylation, and biological properties, Nat. Prod. Rep. 200825, 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. 200952, 5771-5780.

Bleomycin A2

  • D. L. Boger and H. Cai, Bleomycin: synthetic and mechanistic studies, Angew. Chem. Int. Ed. 199938, 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. 2002102, 2477-2496.
  • W. C. Tse and D. L. Boger, Sequence-selective DNA recognition: natural products and nature’s lessons, Chem. Biol. 200411, 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. 200437, 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. 201020, 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. 200311, 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. 200342, 4138-4176.
  • L. R. Whitby and D. L. Boger, Comprehensive peptidomimetic libraries targeting protein-protein interactions, Acc. Chem. Res201245, 1698-1704.

Signal Transduction

  • D. L. Boger and J. Goldberg, Cytokine receptor dimerization and activation: prospects for small molecule agonists, Bioorg. Med. Chem. 20019, 119-124.
  • D. L. Boger, Solution-phase synthesis of combinatorial libraries designed to modulate protein-protein or protein-DNA interactions, Bioorg. Med. Chem. 200311, 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. 20029, 2005-2032.

Vancomycin, Teicoplanin, and Ramoplanin

  • D. L. Boger, Vancomycin, Teicoplanin, and Ramoplanin: Synthetic and Mechanistic Studies, Med. Chem. Rev. 200121, 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.2005105, 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. 201245, 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. 2009105, 465-477.

Vinblastine

  • J. E. Sears and D. L. Boger, Total synthesis of vinblastine, related natural products, key analogues and development of inspired methodology suitable for the systematic study of their structure-function properties, Acc. Chem. Res. 2015, 48, 653-662.        

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. Neurosci20123, 340-348. (Invited mini-review).


Natural Products Total Syntheses:


  • Sendaverine (M. D. Mullican), J. Org. Chem. 198449, 4033-4044.
  • Juncusol (M. D. Mullican), J. Org. Chem. 198449, 4045-4049.
  • Rufescine and Imelutine (C. E. Brotherton), J. Org. Chem. 198449, 4050-4055.
  • Streptonigrin (J. S. Panek), J. Am. Chem. Soc. 1985107, 5745-5754.
  • Lavendamycin (J. S. Panek, S. R. Duff, M. Yasuda), J. Org. Chem. 198550, 5782-5789, 5790-5795.
  • Colchicine (C. E. Brotherton), J. Am. Chem. Soc. 1986108, 6713-6719.
  • PDE-I and PDE-II (R. S. Coleman), J. Am. Chem. Soc. 1987109, 2717-2727.
  • (+)- and ent-(-)-CC-1065 (R. S. Coleman), J. Am. Chem. Soc. 1988110, 1321-1323, 4796-4807.
  • Prodigiosin and Prodigiosene (M. Patel), J. Org. Chem. 198853, 1405-1415.
  • K-13 (D. Yohannes), J. Org. Chem. 198954, 2498-2502.
  • OF4949-III and OF4949-IV (D. Yohannes), J. Org. Chem. 199055, 6000-6017.
  • Deoxybouvardin and RA-VII (D. Yohannes), J. Am. Chem. Soc. 1991113, 1427-1429.
  • cis- and trans-Trikentrin A (M. Zhang), J. Am. Chem. Soc. 1991113, 4230-4234.
  • Combretastatin D-2 (S. Sakya, D. Yohannes), J. Org. Chem. 199156, 4204-4207.
  • (+)- and ent-(-)-Duocarmycin SA (K. Machiya), J. Am. Chem. Soc. 1992114, 10056-10058.
  • d,l- and meso-Isochrysohermidin (C. M. Baldino), J. Am. Chem. Soc. 1993115, 11418-11425.
  • Streptonigrone (K. C. Cassidy, S. Nakahara), J. Am. Chem. Soc. 1993115, 10733-10741.
  • (+)-Piperazinomycin (J. Zhou), J. Am. Chem. Soc. 1993115, 11426-11433.
  • (-)-Sandramycin (J.-H. Chen), J. Am. Chem. Soc. 1993115, 11624-11625; 1996118, 1629-1644.
  • (+)-P-3A (T. Honda, S. L. Colletti, Q. Dang), J. Am. Chem. Soc. 1994116, 82-92.
  • Deglycobleomycin A2 (T. Honda, R. F. Menezes, S. L. Colletti), J. Am. Chem. Soc. 1994116, 5631-5646.
  • Bleomycin A2 (T. Honda), J. Am. Chem. Soc. 1994116, 5647-5656.
  • Bouvardin and O-Methyl Bouvardin (M. A. Patane, J. Zhou), J. Am. Chem. Soc. 1994116, 8544-8556.
  • Natural and ent-Fredericamycin A (O. Hueter, K. Mbiya, M. Zhang), J. Am. Chem. Soc. 1995117, 11839-11849.
  • Granditropone, Grandirubrine, Imerubrine, and Isoimerubrine (K. Takahashi), J. Am. Chem. Soc. 1995117, 12452-12459.
  • Oleamide (B. F. Cravatt), J. Am. Chem. Soc. 1996118, 580-590.
  • (+)- and ent-(-)-Duocarmycin A (J. A. McKie, T. Nishi, T. Ogiku), J. Am. Chem. Soc. 1996118, 2301-2302; 1997119, 311-325.
  • Nothapodytine and (-)-Mappicine (J. Hong), J. Am. Chem. Soc. 1998120, 1218-1222.
  • Ningalin A (C. W. Boyce), J. Am. Chem. Soc. 1999121, 54-62.
  • Lamellarin O and Lukianol A (M. A. Labroli), J. Am. Chem. Soc. 1999121, 54-62.
  • Permethyl Storniamide A (C. A. Sehon), J. Am. Chem. Soc. 1999121, 54-62.
  • Luzopeptins A-C (M. W. Ledeboer, M. Kume), J. Am. Chem. Soc. 1999121, 1098-1099; 11375-11383.
  • Phomazarin (J. Hong, M. Hikota, M. Ishida), J. Am. Chem. Soc. 1999121, 2471-2477.
  • Vancomycin Aglycon (S. Miyazaki, S. H. Kim, J. H. Wu, O. Loiseleur, S. L. Castle), J. Am. Chem. Soc. 1999121, 3226-3227; 10004-10011.
  • HUN-7293 (H. Keim), J. Am. Chem. Soc. 1999121, 6197-6205.
  • Quinoxapeptins A-C (M. W. Ledeboer, M. Kume), J. Am. Chem. Soc. 1999121, 11375-11383.
  • Ningalin B (D. Soenen), J. Org. Chem. 200065, 2479-2483.
  • Distamycin A (B. Fink), J. Am. Chem. Soc. 2000122, 6382-6394.
  • Azatriostin A (J. K. Lee), J. Org. Chem. 200065, 5996-6000.
  • Thiocoraline and BE-22179 (S. Ichikawa), J. Am. Chem. Soc. 2000122, 2956-2957; 2001123, 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. 2000122, 7416-7417; 2001123, 1862-1871.
  • Rubrolone Aglycon (S. Ichikawa, H. Jiang), J. Am. Chem. Soc. 2000122, 12169-12173.
  • Hippadine, Anhydrolycorinium Chloride, Anhydrolycorinone (S. Wolkenberg), J. Org. Chem. 200065, 9120-9124.
  • Fostriecin (S. Ichikawa, W. Zhong), J. Am. Chem. Soc. 2001123, 4161-4167.
  • (-)-Roseophilin (J. Hong), J. Am. Chem. Soc. 2001123, 8515-8519.
  • Ramoplanin A2 and Ramoplanose Aglycon (W. Jiang, J. Wanner, R. J. Lee, P.-Y. Bounaud), J. Am. Chem. Soc. 2002124, 5288-5290; 2003125, 1877-1887.
  • HUN-7293B (Y. Chen), J. Am. Chem. Soc. 2002124, 5431-5440.
  • (+)-Camptothecin (B. Blagg), Tetrahedron 200258, 6343-6349.
  • Anhydrolycorinone (S. Wolkenberg), J. Org. Chem. 200267, 7361-7364.
  • Ristocetin A Aglycon (B. Crowley, Y. Mori, C. McComas, D. Tang), J. Am. Chem. Soc. 2004126, 4310-4317.
  • (+)- and ent-(–)-Yatakemycin (M. Tichenor, D. Kastrinsky), J. Am. Chem. Soc. 2004126, 8396-8398.
  • Ramoplanin A1 and A3 Aglycons (Y. Rew, D. Shin), Proc. Natl. Acad. Sci. USA2004101, 11977-11979.
  • Natural and ent-Minovine (Z. Yuan, H. Ishikawa), Org. Lett. 20057, 741-745.
  • Ningalin D (A. Hamasaki, J. Zimpleman), J. Am. Chem. Soc. 2005127, 10767-10770.
  • (–)- and ent-(+)-Vindoline (H. Ishikawa, Y. Choi, J. Velcicky, G. Elliott, M. Miller), Org. Lett. 20057, 4539-4542; J. Am. Chem. Soc. 2006128, 10596-10612.
  • N-Methylaspidospermidine (H. Ishikawa), J. Am. Chem. Soc. 2006128, 10596-10612.
  • Piericidin A1 and B1 (M. Schnermann), J. Am. Chem. Soc. 2005127, 15704-15705; 2006128, 11799-11807.
  • (–)- and ent-(+)-Vindorosine (G. Elliott, J. Velcicky, H. Ishikawa), Angew. Chem. Int. Ed. 200645, 620-622.
  • [Ψ(CH2NH)Tpg4]Vancomycin Aglycon (B. M. Crowley), J. Am. Chem. Soc. 2006128, 2885-2892.
  • (+)- and ent-(–)-Yatakemycin, (+)- and ent-(–)-Duocarmycin SA (2nd generation, M. Tichenor), J. Am. Chem. Soc. 2006129, 15683-15696.
  • Cytostatin (B. Lawhorn, S. B. Boga), J. Am. Chem. Soc. 2006129, 16720-16732.
  • Ala scan of Ramoplanin (J. Nam, Y. Rew, D. Shin), J. Am. Chem. Soc. 2007129, 8747-8755.
  • Chlorofusin (S. Y. Lee, R. C. Clark), J. Am. Chem. Soc. 2007129, 9860-9861, 2008130, 12355-12369.
  • (+)- and ent-(-)-Vinblastine (H. Ishikawa, D. A. Colby), J. Am. Chem. Soc. 2008130, 420-421.
  • Iso-Duocarmycin SA and iso-yatakemycin (K. S. MacMillan), J. Am. Chem. Soc. 2009131, 1187-1194.
  • Vinblastine, vincristine, and related natural products (H. Ishikawa, D. Colby, S. Seto), J. Am. Chem. Soc. 2009131, 4904-4916.
  • Lycogarubin C and lycogalic acid (J. S. Oakdale) Org. Lett. 201012, 1132-1134.
  • Chloropeptins (complestatin) (J. Garfunkle, H. Shimamura, F. S. Kimball, S. Breazanno) J. Am. Chem. Soc. 2009131, 16036-16038. 2010132, 7776-7783.
  • Phostriecin (aka sultriecin) (C. P. Burke), J. Am. Chem. Soc. 2010132, 2157-2159.
  • Fendleridine (aspidoalbidine) (E. L. Campbell, A. Zuhl), J. Am. Chem. Soc. 2010132, 3009-3012.
  • Vindoline and vindorosine (D. Kato, Y. Sasaki), J. Am. Chem. Soc. 2010132, 3685-3687 and 13533-13544.
  • Compleastatin A and B (S. P. Breazzano) J. Am. Chem. Soc2011133, 18495-18502.
  • [Ψ(C(=NH)NH]Tpg4]Vancomycin Aglycon (A. Okano, J. Xie, J. G. Pierce, R. C. James) J. Am. Chem. Soc. 2012134, 1284-1297.
  • (–)-Aspidospermine and (+)-Spegazzinine (J. P. Lajines, W. Jiang) Org. Lett. 201214, 2078-2081.
  • Kopsinine (J. Xie, A. L. Wolfe), Org. Lett. 201315, 868-870.
  • (–)-Pyrimidoblamic Acid and P-3A (A. S. Duerfeldt), J. Am. Chem. Soc. 2014136, 2119–2125.
  • (–)-Kopsifoline D and (–)-Deoxoapodine (K. Lee),  J. Am. Chem. Soc. 2014, 136, 3312–3317.
  • Vancomycin (A. Nakayama, A. Okano, Y. Feng, J. Collins, K. Collins), Org. Lett. 201416, 3572–3575.
  • (–)-Kopsinine (K. Lee), Tetrahedron 2015, 71, 3741-3746.
  • [Ψ(C(=NH)NH]Tpg4]Vancomycin and Chlorobiphenyl derivative (A. Okano, A. Nakayama, A. Schammel), J. Am. Chem. Soc. 2014136, 13522-13525.
  • [Ψ(C(=S)NH]Tpg4]Vancomycin, [Ψ(C(=NH)NH]Tpg4]Vancomycin, [Ψ(CH2NH]Tpg4]Vancomycin and their (4-Chlorobiphenyl)methyl derivatives (A. Okano, A. Nakayama, K. Wu, E. A. Lindsey, A. W. Schammel) J. Am. Chem. Soc. 2015, 137, 3693-3704.
  • Dihydrolysergic Acid and Dihydrolysergol (K. Lee, Y. B. Poudel) Tetrahedron 2015, 71, 5897-5905.
  • (–)-Vindoline and (+)-4-epi-Vindoline (J. Sears) Org. Lett. 2015, 17, 5460-5463.
  • Methoxatin (C. Glinkerman) J. Am. Chem. Soc. 2016, 138, 12408-12413.