Temperature controlled stereospecific epoxidation of 5-adrosten-3#beta#, 17#beta# -diol diacetate. Preparation of 6#alpha#-and 6#beta#-substituted androstane derivatives

摘要

Reaction of 5-androsten-3#beta#-17#beta#-diol diacetate with m-chloroperbenzoic acid at different temperatures and pH in a biphasic system with NaHCO_3 as a phase transfer catalyst yields corresponding 5#alpah#, 6#beta#- and 5#beta#, 6#beta#-epoxides, which could be separated by column chromatography. Exclusive formation of 5#alpha#, 6#alpha#-epoxide could be obtained at a low temperature (-20 deg C). Epoxides on treatment with different amines lead to stereospecific opening, the amino substituent entering from the opposite side at C-6.