2α,3α-Epoxy-5α-hydroxyandrostan-17-one undergoes rearrangement to form 4-methyloestra-1,3,5(10)-trien-17-one whilst the corresponding 6-ketone affords 1-methyloestra-1,3,5(10)-triene-6,17-dione on treatment with HBr in glacial acetic acid.
J. R. Hanson, J. Chem. Soc. D, 1971, 1119 DOI: 10.1039/C29710001119
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