Bengazoles C-G from the sponge Jaspis sp. Synthesis of the side chain and determination of absolute configuration

Journal of Organic Chemistry

Volumn 61, Issue 12, 1996, Pages 4073-4079

  Searle, Philip A ^a,b   Richter, Rowena K ^a,c   Molinski, Tadeusz F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b FLORIDA ATLANTIC UNIVERSITY   (United States)

^c Shaman Pharmaceuticals Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOTERICIN B; BENGAZOLE C; BENGAZOLE D; BENGAZOLE E; BENGAZOLE F; BENGAZOLE G; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CHIRALITY; CIRCULAR DICHROISM; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; MASS SPECTROMETRY; MINIMUM INHIBITORY CONCENTRATION; NUCLEAR MAGNETIC RESONANCE; SPONGE; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0029953345     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952261a     Document Type: Article

References (30)

1. Lewis, J. R. Nat. Prod. Rep. 1994, 11, 395-418.
2. Lewis, J. R. Nat. Prod. Rep. 1995, 12, 135-163.
3. Faulkner, D. J. Nat. Prod. Rep. 1994, 11, 355-395.
4. Faulkner, D. J. Nat. Prod. Rep. 1995,12, 223-269.
5. Matsunaga, S.; Fusetani, N.; Hashimoto, K.; Koseki, K.; Noma, M. J. Am. Chem. Soc. 1986, 108, 847-849.
6. Kernan, M. R.; Molinski, T. F.; Faulkner, D. J. J. Org. Chem. 1988, 53, 5014-20.
7. Ichiba, T.; Yoshida, W. Y.; Scheuer, P. J.; Higa, T.; Gravalos, D. G. J. Am. Chem. Soc. 1991, 113, 3173-3174.
8. Searle, P. A.; Molinski, T. F. J. Am. Chem. Soc. 1995, 117, 8126-8131.
9. Kobayashi, J.; Kondo, K; Ishibashi, M.; Wälchli, M. R.; Nakamura, T. J. Am. Chem. Soc. 1993, 115, 6661-6665.
10. Kondo, K.; Ishibashi, M.; Kobayashi, J. Tetrahedron 1994, 50, 8355-8362.
11. Adamczeski, M.; Quiñoà, E.; Crews, P. J. Am. Chem. Soc. 1988, 110, 1598-1602.
12. Molinski, T. F. J. Nat. Prod. 1993, 56, 1-8.
13. Rodriguez, J.; Nieto, R. M.; Crews, P. J. Nat. Prod. 1993, 56, 2034-2040.
14. Rudi, A.; Kashman, Y.; Benayahu, Y.; Schleyer, M. J. Nat. Prod. 1994, 57, 829-832.
15. Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511-3515.
16. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
17. Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy: Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983; p 460.
18. Circular Dichroism: Principles and Applications; Nakanishi, K., Berova N., Woody, R. W., Eds.; VCH: New York, 1994; p 570.
19. Wiesler, W. T.; Nakanishi, K. J. Am. Chem. Soc. 1989, 111, 3446-3447.
20. Wiesler, W. T.; Nakanishi, K. J. Am. Chem. Soc. 1990, 112, 5574-5583.
21. Zhao, P.; Zhao, N.; Rele, D. N.; Berova, N.; Nakanishi, K. J. Am. Chem. Soc. 1993, 115, 9313-9314.
22. Zhou, P.; Berova, N.; Wiesler, W. T.; Nakanishi, K. Tetrahedron 1993, 49, 9343-9352.
23. Molinski, T. F. Unpublished results.
24. The choice of L- or D-fucose was arbitrary at this point; however, L-fucose was the less expensive enantioraer.
25. Barton, D. H.; Jang, D. O.; Jaszberenyi, J. C. J. Org. Chem. 1993, 58, 6838-6842.
26. We cannot, of course, rule out the very unlikely possibility of a partial racemate containing ent-3 and, therefore, heterochirality in 1a-g.
27. Loss of the fatty acid side chain, e.g. 3, renders deacyl bengazoles inactive against C. albicans.
28. Hodges, J. C.; Patt, W. C.; Connolly, C. J. J. Org. Chem. 1991, 56, 449-452.
29. Quiñoà, E.; Adamczeski, M.; Crews, P.; Bakus, G. J. J. Org. Chem. 1986, 51, 4494-4497.
30. Searle, P. A.; Molinski, T. F. Tetrahedron 1994, 50, 9893-9908.