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Issue 12, 1969
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A study of the Henbest reduction: the preparation of 3α-hydroxy-5α- and 3β-hydroxy-5β-steroids

Abstract

The reduction of 3-oxo-steroids by a solution of chloroiridic acid and trimethyl phosphite in 90% aqueous propan-2-ol (Henbest reduction) gives axial alcohols in the 5α- or 5β-series and is selective for 3-oxo-groups. Oxo-functions at C-6, C-11, C-12, C-17, and C-20 do not react. This method of reduction has been used as the key step in the synthesis of the ‘allo-tetrahydro’ metabolites of several steroid hormones, and related compounds.

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Article type: Paper
DOI: 10.1039/J39690001653
J. Chem. Soc. C, 1969, 1653-1659

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    A study of the Henbest reduction: the preparation of 3α-hydroxy-5α- and 3β-hydroxy-5β-steroids

    P. A. Browne and D. N. Kirk, J. Chem. Soc. C, 1969, 1653
    DOI: 10.1039/J39690001653

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