Minor and Trace Sterols in Marine Invertebrates. 23. Xestospongesterol and Isoxestospongesterol-First Examples of Quadruple Biomethylation of the Sterol Side Chain

Journal of the American Chemical Society

Volumn 103, Issue 12, 1981, Pages 3606-3608

  Li, Lian Niang ^a   Djerassi, Carl ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009141966     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00402a075     Document Type: Article

References (19)

1. C. Djerassi, N. Theobald, W. C. M. C. Kokke, C. S. Pak, and R. M. K. Carlson, Pure Appl. Chem., 51, 1815-1828 (1979);
2. C. Djerassi, C. Djerassi, in press.
3. For reviews of biosynthesis of sterol side chain, see L. J. Goad, Mar. Nat. Prod.: Chem. Biol. Perspect, 28, 75-172 (1978);
4. E. Lederer, Quart. Rev, Chem. Soc., 23, 453-481 (1969).
5. J. A. Ballantine, A. Lavis, J. C. Roberts, and R. J. Morris, J. Exp. Mar. Biol. Ecol, 30, 29-44 (1977).
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8. S. G. Wyllie, B. A. Amos, and L. T6kes, J. Org. Chem., 42, 725-731 (1977).
9. C. Djerassi, Pure Appl. Chem., 50, 171-184 (1978);
10. I. J. Massey and C. Djerassi, J. Org. Chem., 44, 2448-2456 (1979).
11. M. Bortolotto, J. C. Braekman, D. Daloze, and B. Tursch, Bull. Soc. Chirn. Belg, 87, 539-543 (1978). For stereochemistry, see N. Theobald and C. Djerassi, Tetrahedron Lett, 4369-4372 (1978). We are indebted to Dr. J. C. Braekman for providing the sponge.
12. N. Theobald, R. J. Wells, and C. Djerassi, J. Am. Chem. Soc., 100, 7677-7684 (1978).
13. P. B. Dervan and M. A. Shippey, J. Am. Chem. Soc., 98, 1265-1267 (1976).
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16. L. N. Li and C. Djerassi, to be published.
17. L. N. Li, U. Sjdstrand, and C. Djerassi, J. Am. Chem. Soc., 103, 115-119 (1981).
18. L. N. Li, U. Sjdstrand, and C. Djerassi, to be published.
19. R. M. K. Carlson, C. Tarchini, and C. Djerassi in “Frontiers of Bioorganic Chemistry and Molecular Biology”, S. N. Anachenko, Ed, Pergamon, Oxford, 1980, pp 211-224.