Total synthesis of the originally proposed and revised structures of scleritodermin A

Organic Letters

Volumn 10, Issue 17, 2008, Pages 3765-3768

  Liu, Sheng ^a   Cui, Yong Mei ^a   Nan, Fa Jun ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CYCLOPEPTIDE; KETONE; SCLERITODERMIN A;

ARTICLE; CHEMISTRY; ISOMERISM; SYNTHESIS;

AMIDES; ISOMERISM; KETONES; PEPTIDES, CYCLIC;

EID: 55949131228     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801419m     Document Type: Article

References (22)

1. Schmidt, E. W.; Raventos-Suarez. C.; Bifano, M.; Menendez, A. T.; Fairchild, C. R.; Faulkner, D. J. J. Nat. Prod. 2004, 67, 475.
2. (a) Hagihara, M; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 6570.
3. (b) Wipf, P.; Kim, H. J. Org. Chem. 1993, 58, 5592.
4. (c) Deng, J.; Hamada, Y.; Shioiri, T.; Matsunaga, S.; Fusetani, N. Angew. Chem., Int. Ed. Engl. 1994, 33, 1729.
5. (d) Maryanoff, B. E.; Greco, M. N.; Zhang, H. C.; Andrade-Gordon, P.; Kauffman, J. A.; Nicolaou, K. C.; Liu, A.; Brungs, P. H. J. Am. Chem. Soc. 1995, 117, 1225.
6. (e) Bastiaans, H. M. M.; Van der Baan, J.; Ottenheijm, H. C. J. J. Org. Chem. 1997, 62, 3880.
7. (f) Sowinski, J. A.; Toogood, P. L. Chem. Commun. 1999, 981.
8. (g) Wasserman, H. H.; Zhang, R. Tetrahedron 2002, 58, 6277.
9. Wasserman, H. H.; Ho, W. B. J. Org. Chem. 1994, 59, 4364.
10. Mitsunobu, O.; Yamada, M. Bull. Chem. Soc. Jpn. 1967, 40, 2380.
11. Sellanes, D.; Manta, E.; Serra, G. Tetrahedron Lett. 2007, 48, 1827.
12. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405.
13. Inanaga, J; Hirata, K; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
14. Gibson, F. S.; Bergmeier, S. C.; Rapoport, H. J. Org. Chem. 1994, 59, 3216.
15. Dessolin, M; Guillerez, M. G.; Thieriet, N.; Guibe, F.; Loffet, A. Tetrahedron Lett. 1995, 36, 5741.
16. Corey, E. J.; Gin, D. Y.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 9202.
17. Papanikos, A.; Rademann, J; Meldal, M. J. Am. Chem. Soc. 2001, 123, 2176.
18. Yoshino, H.; Tsuji, M. Chem. Pharm. Bull. 1990, 38, 1735.
19. Itagaki, F.; Shigemori, H.; Ishibashi, M.; Nakamura, T.; Sasaki, T.; Kobayashi, J. J. Org. Chem. 1992, 57, 5540.
20. Chill, L.; Kashman, Y.; Schleyer, M. Tetrahedron. 1997, 53, 16147.
21. 3OH, gradient = 0-100% B in 45 rain). A sample of Scleritodermin A was kindly supplied by Professor Eric Schmidt of Utah University.
22. See Supporting Information for details.