Hydroxy-steroids. Part XVIII. Reactions of 17β-chloro-16α,17α-epoxy-5α-androstane and the preparation of 17β-iodo-16α,17α-epoxy-5α-androstane

Abstract

17β-Chloro- and 17β-iodo-16α,17α-epoxy-5α-androstane are reactive compounds which undergo ready rearrangement into 16-halogeno-17-ketones. On treatment with aluminium chloride the chloro-epoxide undergoes methyl group migration, to give 17-methyl-18-nor-5α-androst-13(17)-en-16-one in 82% yield. The iodo-epoxide, which is unstable, is best obtained (22% yield) by oxidising 17-iodo-5α-androst-16-ene with peroxylauric acid in benzene.