Total Synthesis of the Depsipeptide FR-901375

Journal of Organic Chemistry

Volumn 68, Issue 23, 2003, Pages 8902-8905

  Chen, Yanping ^a   Gambs, Celine ^a   Abe, Yoshito ^a   Wentworth Jr , Paul ^a   Janda, Kim D ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MACROLACTONIZATION;

FERMENTATION; SYNTHESIS (CHEMICAL);

POLYPEPTIDES;

3 HYDROXY 7 MERCAPTO 4 HEPTENOIC ACID; ACID; BICYCLO COMPOUND; DEPSIPEPTIDE; FR 901228; FR 901375; LACTONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DEPROTECTION REACTION; DISULFIDE BOND; FERMENTATION; MITSUNOBU REACTION; PEPTIDE SYNTHESIS; PRECURSOR; PSEUDOMONAS; PSEUDOMONAS CHLOROAPHIS;

DEPSIPEPTIDES; PEPTIDES, CYCLIC; PSEUDOMONAS;

EID: 0242660847     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034765b     Document Type: Article

References (25)

1. Fujisawa Pharmaceutical Co., Ltd., Japan. Jpn. Kokai Tokkyo Koho JP, 03141296, 1991.
2. (a) Ueda, H.; Nakajima, H.; Hori, Y.; Fujita, T.; Nishimura, M.; Goto, T.; Okuhara, M. J. Antibiot. 1994, 47, 301.
3. (b) Shigematsu, N.; Ueda, H.; Takase, S.; Tanaka, H.; Yamamoto, K.; Tada, T. J. Antibiot. 1994, 47, 311.
4. (c) Ueda, H.; Manda, T.; Matsumoto, S.; Mukumoto, S.; Nishigaki, F.; Kawamura, I.; Shimomura, K. J. Antibiot. 1994, 47, 315.
5. (a) Blanchard, F.; Kinzie, E.; Wang, Y.; Duplomb, L.; Godard, A.; Held, W. A.; Asch, B. B.; Baumann, H. Oncogene 2002, 21, 6264.
6. (b) Nakajima, H.; Kim, Y. B.; Terano, H.; Yoshida, M.; Horinouchi, S. Exp. Cell Res. 1998, 241, 126.
7. Skov, S. PCT Int. Appl., WO 0142282 Al 20010614, 2001.
8. Vigushi, D. M. Curr. Opin. Invest. Drugs 2002, 1396.
9. Li, K. W.; Wu, J.; Xing, W.; Simon, J. A. J. Am. Chem. Soc. 1996, 118, 7237.
10. Mitsunobu, O. Synthesis 1981, 1.
11. (a) Carpino, L. A.; Han, G. Y. J. Org. Chem. 1972, 37, 3.
12. (b) Carpino, L. A. Acc. Chem. Res. 1987, 20, 401.
13. Hakimelahi, G.; Jarrahpour, A. A. Helv. Chim. Acta 1989, 72, 1501.
14. Niu, C.; Petterson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014.
15. Smrcina, M.; Lorenc, M.; Hanus, V.; Sedmera, P.; Kocovsky, P. J. Org. Chem. 1992, 57, 1917.
16. Gazal, S.; Gellerman, G.; Glukhov, E.; Gilon, C. J. Pept. Res. 2001, 58, 527. In this paper, aldehyde 12 was prepared from 3-bromopropionic acid in three steps.
17. Guz, N. R.; Phillips, A. J. Org. Lett. 2002, 2253.
18. The absolute configuration of aldol product was tentatively assigned based on both Phillips' model and by the optical rotation of the hydrolyzed product.
19. (a) Evans, D. A.; Sjogren, E. B.; Weber, A. E.; Conn, R. E. Tetrahedron Lett. 1987, 28, 39.
20. (b) Evans, D. A.; Carter, P. H.; Carreira, E. M.; Charette, A. B.; Prunet, J. A.; Lautens, M. J. Am. Chem. Soc. 1999, 121, 7540.
21. Crude NMR shows only one single diastereomer. The absolute configuration is based on Evans' model.
22. Wang, Y.-C.; Yan, T.-H. Chem. Commun. 2000, 545.
23. 2) in ref 6.
24. Kamber, B.; Hartmann, A.; Eisler, K.; Riniker, B.; Rink, H.; Sieber, P.; Rittel, W. Helv. Chem. Acta 1980, 63, 899.
25. Newton, R. F.; Reynolds, D. P.; Finch, M. A. W.; Kelly, D. R.; Roberts, S. M. Tetrahedron Lett. 1979, 3981. Care should be taken when using 48% HF aqueous solution (see SI).