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Preparation of steroidal 5 beta 6 beta epoxides and their oxidation by chromium trioxide


, : Preparation of steroidal 5 beta 6 beta epoxides and their oxidation by chromium trioxide. Journal of the Chemical Society Perkin Transactions I (7): 2001-2004

Reaction of 3.alpha.-chloroandrost-5-en-17-one with m-chloroperbenzoic acid affords the 5.beta.,6.beta.-epoxide. This is accomplished by some Baeyer-Villiger oxidation at C-17. The 3.alpha.-chlorine atom can be removed by hydrogenolysis with tributyltin hydride. Although the unsubstituted 5.beta.,5.beta.-epoxide is oxidized by chromium trioxide to the 5.alpha.-hydroxy 6-ketone, the 3.alpha.-chloro 5.beta.,6.beta.-epoxide is unreactive.

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