Enantioselective total synthesis of (+)-duocarmycin A, epi-(+)-duocarmycin A, and their unnatural enantiomers

Journal of the American Chemical Society

Volumn 118, Issue 9, 1996, Pages 2301-2302

  Boger, Dale L ^a   McKie, Jeffrey A ^a   Nishi, Takahide ^a   Ogiku, Tsuyoshi ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DUOCARMYCIN A;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; STEREOCHEMISTRY;

EID: 0029871620     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953777e     Document Type: Article

References (26)

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3. Takahashi, I.; Takahashi, K.; Ichimura, M.; Morimoto, M.; Asano, K.; Kawamoto, I.; Tomita, F.; Nakano, H. J. Antibiot. 1988, 41, 1915. Yasuzawa, T.; Iida, T.; Muroi, K.; Ichimura, M.; Takahashi, K.; Sano, H. Chem. Pharm. Bull. 1988, 36, 3728. Yasuzawa, T.; Muroi, K.; Ichimura, M.; Takahashi, I.; Ogawa, T.; Takahashi, K.; Sano, H.; Saitoh. Y. Chem. Pharm. Bull. 1995, 43, 378.
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8. Boger, D. L.; Johnson, D. S. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 3642. Boger, D. L. Acc. Chem. Res. 1995, 28, 20. Boger, D. L. Chemiracts: Org. Chem. 1991, 4, 329.
9. Boger, D. L.; Johnson, D. S. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 3642. Boger, D. L. Acc. Chem. Res. 1995, 28, 20. Boger, D. L. Chemiracts: Org. Chem. 1991, 4, 329.
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12. For the nondiastereoselective synthesis of duocarmycin A and its isomers, see: Fukuda, Y.; Itoh, Y.; Nakatani, K.; Terashima, S. Tetrahedron 1994, 50, 2793. Fukuda, Y.; Nakatani, K.; Terashima, S. Tetrahedron 1994, 50, 2809.
13. For the nondiastereoselective synthesis of duocarmycin A and its isomers, see: Fukuda, Y.; Itoh, Y.; Nakatani, K.; Terashima, S. Tetrahedron 1994, 50, 2793. Fukuda, Y.; Nakatani, K.; Terashima, S. Tetrahedron 1994, 50, 2809.
14. (+)- and em-(-)-duocarmycin SA: Boger, D. L.; Machiya, K. J. Am. Chem. Soc. 1992, 114, 10056. Boger, D. L.; Machiya, K.; Hertzog, D. L.; Kitos, P. A.; Holmes, D. J. Am. Chem. Soc. 1993, 115, 9025. (±)-Duocarmycin SA: Muratake, H.; Abe, I.; Natsume, M. Tetrahedron Lett. 1994, 35, 2573. (+)-Duocarmycin SA: Muratake, H.; Matsumura, N.; Natsume, M. Chem. Pharm. Bull. 1995, 43, 1064.
15. (+)- and em-(-)-duocarmycin SA: Boger, D. L.; Machiya, K. J. Am. Chem. Soc. 1992, 114, 10056. Boger, D. L.; Machiya, K.; Hertzog, D. L.; Kitos, P. A.; Holmes, D. J. Am. Chem. Soc. 1993, 115, 9025. (±)-Duocarmycin SA: Muratake, H.; Abe, I.; Natsume, M. Tetrahedron Lett. 1994, 35, 2573. (+)-Duocarmycin SA: Muratake, H.; Matsumura, N.; Natsume, M. Chem. Pharm. Bull. 1995, 43, 1064.
16. (+)- and em-(-)-duocarmycin SA: Boger, D. L.; Machiya, K. J. Am. Chem. Soc. 1992, 114, 10056. Boger, D. L.; Machiya, K.; Hertzog, D. L.; Kitos, P. A.; Holmes, D. J. Am. Chem. Soc. 1993, 115, 9025. (±)-Duocarmycin SA: Muratake, H.; Abe, I.; Natsume, M. Tetrahedron Lett. 1994, 35, 2573. (+)-Duocarmycin SA: Muratake, H.; Matsumura, N.; Natsume, M. Chem. Pharm. Bull. 1995, 43, 1064.
17. (+)- and em-(-)-duocarmycin SA: Boger, D. L.; Machiya, K. J. Am. Chem. Soc. 1992, 114, 10056. Boger, D. L.; Machiya, K.; Hertzog, D. L.; Kitos, P. A.; Holmes, D. J. Am. Chem. Soc. 1993, 115, 9025. (±)-Duocarmycin SA: Muratake, H.; Abe, I.; Natsume, M. Tetrahedron Lett. 1994, 35, 2573. (+)-Duocarmycin SA: Muratake, H.; Matsumura, N.; Natsume, M. Chem. Pharm. Bull. 1995, 43, 1064.
18. Boger, D. L.; Zarrinmayeh, H. J. Org. Chem. 1990, 55, 1379.
19. 3, 0 to 25 °C, 4 h, 84%.
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21. 3
22. This latter procedure, which benefits from an unusually large separation, was employed to further enrich the mixture obtained from ADH or to resolve racemic material and dependably assured the optical purity of the samples (>99.9% ee).
23. Boger, D. L.; Nishi, T. Bioorg. Med. Chem. 1995, 3, 67.
24. The minor diastereomer (10-14%) was readily removed upon chromatography.
25. Boger, D. L.; Ishizaki, T.; Zarrinmayeh, H.; Kitos, P. A.; Suntornwat, O. J. Org. Chem. 1990, 55, 4499.
26. 3).