Total Synthesis of (+)-Octalactins A and B: Unusual Metabolites from a Marine Microbe

Journal of the American Chemical Society

Volumn 116, Issue 18, 1994, Pages 8378-8379

  McWilliams, J Chris ^a   Clardy, Jon ^a  

^a Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOTOXIC AGENT; OCTALACTIN A; OCTALACTIN B; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; HUMAN; HUMAN CELL; INVERTEBRATE; STREPTOMYCES;

EID: 0027972829     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00097a060     Document Type: Article

References (21)

1. Tapiolas, D. M.; Roman, M.; Fenical, W.; Stout, T. J.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 4682-4683.
2. Buszek, K. R.; Sato, N.; Jeong, Y. J. Am. Chem. Soc. 1994, 116, 5511-5512.
3. Takai, K.; Hotta, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1978, 2417-2420.
4. Narasaka, K.; Soai, K.; Aikawa, Y.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1976, 49, 779-783.
5. Urech, R. J. J. Chem. Soc., Chem. Commun. 1984, 989-990.
6. Asaoka, M.; Takei, H.; Tetrahedron Lett. 1987, 28, 6343-6346.
7. Herrman, J. L.; Schlessinger, R. H. J. Chem. Soc., Chem. Commun. 1973, 711-712.
8. Grieco, P. A. Synthesis 1975, 67-82.
9. 4, as has been observed in a related system, in which a β-hydroxyl group was generated upon reduction: Rajaskekhar, B.; Kaiser, E. T. J. Org. Chem. 1985, 50, 5480-5484.
10. Brown, H. C.; Narahimhon, S.; Choi, Y. M. J. Org. Chem. 1982, 47, 4702-4708.
11. Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1993, 58, 3791-3793.
12. Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651-1660.
13. Veysoglu, T.; Mitscher, L. A. Tetrahedron Lett. 1981, 22, 1299-1302.
14. van Boekel, C. A. A.; Beetz, T. Tetrahedron Lett. 1983, 24, 3775-3778.
15. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4156-4158.
16. Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 391-394.
17. Eis, M. J.; Ganem, B. J. Am. Chem. Soc. 1984, 106, 3693-3694.
18. Uchida, K.; Utimoto, K.; Nozaki, H. Tetrahedron 1977, 33, 2987-2992.
19. Uchida, K.; Utimoto, K.; Nozaki, H. J. Org. Chem. 1976, 41, 2941-2942.
20. Miller, R. B.; McGarvey, G. J. Org. Chem. 1979, 44, 4623-4633.
21. Miller, R. B.; McGarvey, G. J. Org. Chem. 1978, 43, 4424-4431.