
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.
Bleomycin A2
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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.
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 proteinprotein or proteinDNA 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.
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 proteinprotein or proteinDNA 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.
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. Hüter, 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.
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