Abstract
Expoxidation of cholesta-5,8-dien-3?-yl acetate (1) with peracids takes place preferentially at the more highly substituted ?8-olefinic double bond to give: (a) with monoperphthalic acid, 8?,9?-epoxycholest-5-en-3?-yl acetate (2) (in 39 % yield) and 9?-hydroxy-5?,6?-epoxycholest-8(14)-en-3?-yl acetate (3) (in 30 % yield); and (b) with m-chloroperbenzoic acid, the 8?,9?-epoxide 2 (64 %) and 5?,6?-epoxy derivative 3 (20%). Some chemical transformations of the obtained epoxides are described.
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