Synthesis of polyhydroxysterols (IV): synthesis of 24-methylene-cholesta-3beta,5alpha,6beta,19-tetrol, a cytotoxic natural hydroxylated sterol.
The cytotoxic, polyhydroxylated sterol 24-methylene-cholesta-3beta,5alpha,6beta,19-tetrol (1), previously isolated from the soft corals Nephthea albida and N. tiexieral verseveldt, was synthesized using stigmasterol as the starting material by 10 steps in 9% overall yield. The spectral data and physical constants of 1 were identical with those of the natural product. This is the first report of the synthesis of 1.
Lu
Weigang
W
School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, China.
Zeng
Longmei
L
Su
Jingyu
J
D000818:Animals; D002455:Cell Division / Q000187:drug effects; D045744:Cell Line, Tumor; D002777:Cholestanols / Q000138:chemical synthesis* / Q000494:pharmacology; D051379:Mice; D008968:Molecular Conformation; D013261:Sterols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
C466905:24-methylene-cholestane-3, 5,6,19-tetrol; D002777:Cholestanols; D013261:Sterols