Preparation of steroidal 5β,6β-epoxides and their oxidation by chromium trioxide
Abstract
Reaction of 3α-chloroandrost-5-en-17-one with m-chloroperbenzoic acid affords the 5β,6β-epoxide. This is accompanied by some Baeyer-Villiger oxidation at C-17. The 3α-chlorine atom can be removed by hydrogenolysis with tributyltin hydride. Although the unsubstituted 5β,5β-epoxide is oxidized by chromium trioxide to the 5α-hydroxy 6-ketone, the 3α-chloro 5β,6β-epoxide is unreactive.