The epoxide ring in steroidal trans-αβ, and βγ-epoxy-alcohols is cleaved by sodium borohydride in refluxing methanol to give the corresponding methoxyhydrins, in contrast to the cis-epoxy-alcohols which remain unchanged. The steric requirements of the reaction and a mechanism involving the intermediate formation of a boron complex with the substrate are discussed.
M. Weissenberg, P. Krinsky and E. Glotter, J. Chem. Soc., Perkin Trans. 1, 1978, 565 DOI: 10.1039/P19780000565
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