Co-Authors:
Weissenberg, M., Department of Organic Chemistry, The Weizmann Institute of Science, Rehovot, Israel
Lavie, D., Department of Organic Chemistry, The Weizmann Institute of Science, Rehovot, Israel
Glotter, E., Department of Organic Chemistry, The Weizmann Institute of Science, Rehovot, Israel
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. © 1973.
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