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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.
J. R. Hanson and A. Truneh, J. Chem. Soc., Perkin Trans. 1, 1988, 2001 DOI: 10.1039/P19880002001
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