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Chromium trioxide oxidation of steroidal 3β-acetoxy-4α,5α-epoxides affords products in which the acetoxy group has migrated to the 4β-position whilst oxidation of the isomeric 4β,5β-epoxides affords 5α-hydroxy-4-ketones without rearrangement. The effect of 3-chloro and 6β-acetoxy substituents is explored.
N. Flaih, J. R. Hanson and P. B. Hitchcock, J. Chem. Soc., Perkin Trans. 1, 1991, 1085 DOI: 10.1039/P19910001085
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