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Issue 0, 1972
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Aromatization of some 4,5-epoxy-3-hydroxysteroids


Treatment of the epimeric 17β-acetoxy-4,5-epoxyandrostan-3β-ols with hydrogen bromide in glacial acetic acid gave 17β-acetoxy-4-methyloestra-1,3,5(10)-triene by a dienol–benzene pathway. Under the same conditions 3β-hydroxy-4β,5β-epoxyandrostane-6,17-dione gave 1-methyloestra-1,3,5(10)-triene-6,17-dione, whilst 3β,17β-diacetoxy-4α,5α-epoxyandrostan-11-one gave a low yield of 17β-acetoxy-4-methyloestra-1,3,5(10)-trien-11-one, revealing that the influence of the carbonyl groups at C-6 and C-11 on this reaction is similar to that on the dienone–phenol rearrangement.

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J. Chem. Soc., Perkin Trans. 1, 1972, 1889-1891
Article type

Aromatization of some 4,5-epoxy-3-hydroxysteroids

D. Baldwin and J. R. Hanson, J. Chem. Soc., Perkin Trans. 1, 1972, 1889
DOI: 10.1039/P19720001889

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