Total synthesis of salinamide A: A potent anti-inflammatory bicyclic depsipeptide

Angewandte Chemie - International Edition

Volumn 47, Issue 19, 2008, Pages 3614-3617

  Tan, Li ^a   Ma, Dawei ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Anti inflammatory agent; Depsipeptide; Epoxides; Macrocyclization; Total synthesis

Indexed keywords

ANTI-INFLAMMATORY AGENT; DEPSIPEPTIDE; EPOXIDES; MACROCYCLIZATION; TOTAL SYNTHESIS;

DEPSIPEPTIDE; NONSTEROID ANTIINFLAMMATORY AGENT; SALINAMIDE A;

ARTICLE; STREPTOMYCES; SYNTHESIS;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; DEPSIPEPTIDES; STREPTOMYCES;

EID: 44049095562     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800397     Document Type: Article

References (30)

1. a) J. A. Trischman, D. M. Tapiolas, P. R. Jensen, R. Dwight, W. Fenical, T. C. McKee, C. M. Ireland, T. J. Stout, J. Clardy, J. Am. Chem. Soc. 1994, 116, 757;
2. b) B. S. Moore, J. A. Trischman, P. R. Jensen, W. Fenical, J. Org. Chem. 1999, 64, 1145.
3. S. Miao, M. R. Anstee, K. LaMarco, J. Mattew, L. H. Huang, M. M. Brasseur, J. Nat. Prod. 1997, 60, 858.
4. M. K. Renner, Y.-C. Shen, X.-C. Cheng, P. R. Jensen, W. Frankmoelle, C. A. Kauffman, W. Fenical, E. Lobkovsky, J. Clardy, J. Am. Chem. Soc. 1999, 121, 11273.
5. a) A. Randazzo, G. Bifulco, C. Giannini, M. Bucci, C. Debitus, G. Cirino, L. Gomez-Paloma, J. Am. Chem. Soc. 2001, 123, 10870;
6. b) C. Della Monica, A. Randazzo, G. Bifulco, P. Cimino, M. Aquino, I. Izzo, F. De Riccardis, L. Gomez-Paloma, Tetrahedron Lett. 2002, 43, 5707.
7. a) H. Sugiyama, T. Shioiri, F. Yokokawa, Tetrahedron Lett. 2002, 43, 3489;
8. b) S.-J. Wen, H.-W. Zhang, Z.-J. Yao, Tetrahedron Lett. 2002, 43, 5291;
9. c) J. E. Tarver, M. M. Joullie, J. Org. Chem. 2004, 69, 815;
10. d) S.-J. Wen, Z.-J. Yao, Org. Lett. 2004, 6, 2721.
11. a) B. B. Snider, J. R. Duvall, Tetrahedron Lett. 2003, 44, 3067;
12. b) C. Della Monica, N. Maulucci, F. De Riccardis, I. Izzo, Tetrahedron: Asymmetry 2003, 14, 3371;
13. c) I. Izzo, E. Avallone, L. D. Corte, N. Maulucci, F. De Riccardis, Tetrahedron: Asymmetry 2004, 15, 1181;
14. d) S. Hara, K. Makino, Y. Hamada, Tetrahedron 2004, 60, 8031;
15. e) S. Yu, X. Pan, X. Lin, D. Ma, Angew. Chem. 2005, 117, 137;
16. Angew. Chem. Int. Ed. 2005, 44, 135;
17. f) K. C. Nicolaou, D. W. Kim, D. Schlawe, D. E. Lizos, R. G. de Noronha, D. A. Longbottom, Angew. Chem. 2005, 117, 5005;
18. Angew. Chem. Int. Ed. 2005, 44, 4925;
19. g) S. Hara, K. Makino, Y. Hamada, Tetrahedron Lett. 2006, 47, 1081;
20. h) K. C. Nicolaou, D. E. Lizos, D. W. Kim, D. Schlawe, R. G. de Noronha, D. A. Longbottom, M. Rodriquez, M. Bucci, G. Cirino, J. Am. Chem. Soc. 2006, 128, 4460;
21. i) S. Yu, X. Pan, D. Ma, Chem. Eur. J. 2006, 12, 6572.
22. B. S. Moore, S. Seng, Tetrahedron Lett. 1998, 39, 3915.
23. W. R. Roush, B. J. Brown, J. Org. Chem. 1993, 58, 2151.
24. B. E. Rossiter, T. Katsuki, K. B. Sharpless, J. Am. Chem. Soc. 1981, 103, 464.
25. a) M. Caron, K. B. Sharpless, J. Org. Chem. 1985, 50, 1557;
26. b) K. Kazuhiro, F. Yoshiro, Y. Hiroshi, O. Junzo, Tetrahedron 1999, 55, 14381.
27. C. A. Marhefka, W. Gao, K. Chung, J. Kim, Y. He, D. Yin, C. Bohl, J. T. Dalton, D. D. Miller, J. Med. Chem. 2004, 47, 993.
28. S. J. Wittenberger, M. A. McLaughlin, Tetrahedron Lett. 1999, 40, 7175.
29. W. Oppolzer, C. Starkemann, I. Rodriguez, G. Bernardinelli, Tetrahedron Lett. 1991, 32, 61.
30. K. A. Scheidt, H. Chen, B. C. Follows, S. R. Chemler, D. S. Coffey, W. R. Roush, J. Org. Chem. 1998, 63, 6436.