Relative and absolute stereochemistry of mycalolides, bioactive macrolides from the marine sponge Mycale magellanica

Journal of the American Chemical Society

Volumn 121, Issue 23, 1999, Pages 5605-5606

  Matsunaga, Shigeki ^a   Liu, Ping ^b   Celatka, Cassandra A ^b   Panek, James S ^b   Fusetani, Nobuhiro ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b Metcalf Center for Science and Engineering   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; MACROLIDE; MYCALOLIDE A; MYCALOLIDE B; MYCALOLIDE C; NATURAL PRODUCT; SWINHOLIDE A; SWINHOLIDE B; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG ISOLATION; MARINE ENVIRONMENT; REACTION ANALYSIS; SPONGE (PORIFERA); STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

MYCALE MAGELLANICA;

EID: 0033575053     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990817w     Document Type: Article

References (23)

1. Bioactive Marine Metabolites. 94. Part 93: Fusetani, N.; Warabi, K.; Nogata, Y.; Nakao, Y.; Matsunaga, S. Tetrahedron Lett. In press.
2. Bioactive Marine Metabolites. 94. Part 93: Fusetani, N.; Warabi, K.; Nogata, Y.; Nakao, Y.; Matsunaga, S. Tetrahedron Lett. In press.
3. Other trisoxazole-containing macrolides are (a) kabiramides A-E (Matsunaga, S.; Fusetani, N.; Hashimoto, K.; Koseki, K.; Noma, M.; Noguchi, H.; Sankawa, U. J. Org. Chem. 1989, 54, 1360-1363), (b) ulapualides A and B (Roesener, J. A.; Scheuer, P. J. J. Am. Chem. Soc. 1986, 108, 846-847), halichondramides (Kernan, M. R.; Molinski, T. F.; Faulkner, J. D. J. Org. Chem. 1988, 53, 5014-5020), and (d) jaspisamides A-C (Kobayashi, J.; Murata, O.; Shigemori, H. J. Nat. Prod. 1993, 56, 787-791).
4. Other trisoxazole-containing macrolides are (a) kabiramides A-E (Matsunaga, S.; Fusetani, N.; Hashimoto, K.; Koseki, K.; Noma, M.; Noguchi, H.; Sankawa, U. J. Org. Chem. 1989, 54, 1360-1363), (b) ulapualides A and B (Roesener, J. A.; Scheuer, P. J. J. Am. Chem. Soc. 1986, 108, 846-847), halichondramides (Kernan, M. R.; Molinski, T. F.; Faulkner, J. D. J. Org. Chem. 1988, 53, 5014-5020), and (d) jaspisamides A-C (Kobayashi, J.; Murata, O.; Shigemori, H. J. Nat. Prod. 1993, 56, 787-791).
5. Other trisoxazole-containing macrolides are (a) kabiramides A-E (Matsunaga, S.; Fusetani, N.; Hashimoto, K.; Koseki, K.; Noma, M.; Noguchi, H.; Sankawa, U. J. Org. Chem. 1989, 54, 1360-1363), (b) ulapualides A and B (Roesener, J. A.; Scheuer, P. J. J. Am. Chem. Soc. 1986, 108, 846-847), halichondramides (Kernan, M. R.; Molinski, T. F.; Faulkner, J. D. J. Org. Chem. 1988, 53, 5014-5020), and (d) jaspisamides A-C (Kobayashi, J.; Murata, O.; Shigemori, H. J. Nat. Prod. 1993, 56, 787-791).
6. Other trisoxazole-containing macrolides are (a) kabiramides A-E (Matsunaga, S.; Fusetani, N.; Hashimoto, K.; Koseki, K.; Noma, M.; Noguchi, H.; Sankawa, U. J. Org. Chem. 1989, 54, 1360-1363), (b) ulapualides A and B (Roesener, J. A.; Scheuer, P. J. J. Am. Chem. Soc. 1986, 108, 846-847), halichondramides (Kernan, M. R.; Molinski, T. F.; Faulkner, J. D. J. Org. Chem. 1988, 53, 5014-5020), and (d) jaspisamides A-C (Kobayashi, J.; Murata, O.; Shigemori, H. J. Nat. Prod. 1993, 56, 787-791).
7. Fusetani, N.; Yasumuro, K.; Matsunaga, S.; Hashimoto, K. Tetrahedron Lett. 1989, 30, 2809-2812.
8. Rashid, M. A.; Gustafson, K. R.; Cardellina II, J. H.; Boyd, M. R. J. Nat. Prod. 1995, 58, 1120-1125.
9. Matsunaga, S.; Sugawara, T.; Fusetani, N. J. Nat. Prod. 1998, 61, 1164-1167. Compounds 1-6 were shown to possess identical absolute stereochemistry on the basis of the advanced Mosher analysis which revealed the 3S stereochemistry (unpublished results).
10. Saito, S.; Watabe, S.; Ozaki, H.; Fusetani, N.; Karaki, H. J. Biol. Chem. 1994, 269, 29710-29714.
11. Ayscough, K. R.; Stryker, J.; Pokala, N.; Sanders, M.; Crews, P.; Drubin, D. G. J. Cell Biol. 1997, 137, 399-416 and references therein.
12. Smith, C. D.; Carmeli, S.; Moore, R. E.; Patterson, G. M. L. Cancer Res. 1993, 53, 1343-1347.
13. Bubb, M. R.; Spector, I.; Bershadsky, A. D.; Korn, E. D. J. Biol. Chem. 1995, 270, 3463-3466.
14. Suenaga, K.; Kamei, N.; Okugawa, Y.; Takagi, M.; Akao, A.; Kigoshi, H.; Yamada, K. Bioorg. Med. Chem. Lett. 1997, 7, 269-274 and references therein.
15. Chattopadhyay, S. K.; Pattenden, G. Tetrahedron Lett. 1998, 39, 6095-6098.
16. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938.
17. 1H NMR data of 7, see Table 1 of the Supporting Information.
18. Otani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
19. For experimental details of the degradation sequences, see the Supporting Information.
20. Acetal 17 was synthesized according to the described procedure; see: Panek, J. S.; Beresis, R. T.; Celatka, C. A. J. Org. Chem. 1996, 61, 6469-6470.
21. Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447-6449.
22. Matsunaga, S.; Liu, P.; Celatka, C. A.; Panek, J. S.; Fusetani, N. Unpublished results. The full details of these studies will be reported at a later time.
23. 11 As a result of the current degradation studies, a discrepancy in the stereochemistry has arisen.