12,13-Epoxy-C-nor-D-homosteroids. I. The synthesis and stereochemistry of 17.ALPHA.-acetyl-12,13-epoxyetiojervanes.
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概要
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Several 11-substituted 17α-acetyl-12,13-epoxyetiojervanes were prepared from jervine. Jervine was degraded by a known process into (17<I>E</I>)-17-ethyletiojerva-4,12,17(20)-triene-3,l 1-dione, which on epoxidation followed by acid treatment gave 17α-ethyletiojerva-4,12-diene-3,l 1,20-trione as the main product. Acetalization of the carbonyl groups, at C<SUB>3</SUB> and C<SUB>20</SUB> of the triketone and subsequent hydride reduction produced two 11-epimeric alcohols, which on hydrolysis afforded 17α-ethyl-11α-hydroxyetiojerva-4,12-diene-3,20-dione and its 11β-hydroxy epimer. These alcohols and their acetates were oxidized with perbenzoic acid and/or <I>t</I>-butyl hydroperoxide to give the epoxides. The structure and configuration of these epoxides and the synthetic intermediates were determined on the basis of the chemical and spectral evidence.
- 公益社団法人 日本化学会の論文
著者
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Murai Akio
Department Of Chemistry Faculty Of Science Hokkaido University
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Masamune Tadashi
Department Of Chemistry Faculty Of Science Hokkaido University
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Sasamori Hiroshi
Department of Chemistry, Faculty of Science, Hokkaido University
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