Treatment of 3α,5-cyclo-5α-androst-6-en-17-one with m-chloroperbenzoic acid affords 3β,7α-dihydroxyandrost-5-en-17-one, 6β,7α-dihydroxy-3α,5-cyclo-5α-androstan-17-one, their 3β- and 6β-m-chlorobenzoates, and the 6β-methoxy-7α-hydroxy-cyclo-steroid. The unstable 6α,7α-epoxy-3α,5-cyclo-5α-androstan-17-one was obtained by epoxidation in ether. A similar range of solvent-dependent produts was obtained in the cholestane series.
R. C. Cambie, P. W. Thomas and J. R. Hanson, J. Chem. Soc., Perkin Trans. 1, 1975, 323 DOI: 10.1039/P19750000323
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