A study of the Henbest reduction: the preparation of 3α-hydroxy-5α- and 3β-hydroxy-5β-steroids
- 1 January 1969
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- No. 12,p. 1653-1659
- https://doi.org/10.1039/j39690001653
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.Keywords
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