Abstract
Treatment of 1,2-epoxy-3-ketosteroids with tosylhydrazine and sodium borohydride in methanol lead to mixtures consisting of (i) ring A seco-acetylenic alcohols, (ii) methoxyhydrins formed by opening of the epoxide ring following the carbonyl reduction, and (iii) an epoxy-3,3-di- methylketal. For the corresponding 4-methylene derivative, the ring A fragmentation product was found to be the conjugated en-yne 8a. Reduction of these epoxyketones with sodium borohydride alone affords mixtures of cis- and trans epoxyalcohols; the cis derivatives were unaffected by heating with sodium borohydride in methanol, whereas the trans were converted into the corresponding diaxial methoxyhydrins.
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