Abstract
3β,14β-Dihydroxyandrost-5-en-17-one has been prepared from 3β-acetoxy-5α,6β-dichloroandrost-14-en-17-one by epoxidation at Δ14 and subsequent rearrangement of the resulting oxide to give the 14β-hydroxy-Δ15-17-ketone. Removal of the 5α,6β-chlorine atoms from this ketone followed by reduction at Δ15 gave the required product. The direct oxidation of 3β-acetoxy-5α,6β-dichloroandrostan-17-one with chromic anhydride in acetic acid to give the corresponding 14α-hydroxy-derivative has been investigated. It has been found that for a successful oxidation to take place it is necessary to have hydrobromic acid present in the reaction mixture. Oxidation by chromyl acetate, however, offers an improved route to the 14α-hydroxy-steroid.
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