Abstract
The previously unknown steroids 5, 22, 24(28)-ergostatriene-3β-yl-acetate, 5, 22, 24-ergostatriene-3β-yl acetate, 5, 7, 22, 24-ergostatetrene-3β-yl-acetate, and 4, 22, 24(28Z)-stigmastatriene-3p-yl-acetate have been synthesized. The naturally occurring 5, 7, 22, 24(28)-ergostatetraene-3β-ol has been prepared for the first time starting from stigmasterol and has been proven to be identical with the sterol isolated from Saccharomyces cerevisiae. The synthetic sequence developed involved a new and highly selective method for specific bromination of the 5,6 double bond of stigmasteryl acetate. The effect that several new side chain groups exert on the chemical shift (NMR) the angular Me groups has been determined.
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