Synthesis of Epimeric 6-Deuterio-4-cholesten-3-ones
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概要
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In order to clarify the stereochemistry of hydrogen transfer from C-4 to C-6 during enzymatic transformation of cholesterol into cholestenone, the title compounds stereospecifically labeled with deuterium have been synthesized as an authentic specimen. The stereospecific labeling at 6β was attained by trans-diaxial opening of the 5α, 6α-oxido ring with lithium aluminum deuteride. Oxidation with chromium trioxide followed by dehydration with p-toluenesulfonic acid provided 6β-d_1-cholestenone (4a). In the similar fashion 6β-d_1-cholestenone (4b) was prepared from 6β-d_1-3α, 5-cyclo-5α-cholestan-6α-ol (6) by way of 6-d_1-cholesteryl acetate (7).
- 公益社団法人日本薬学会の論文
- 1977-11-25
著者
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細田 宏
Pharmaceutical Institute Tohoku University
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池川 繁男
Pharmaceutical Institute, Tohoku University
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南原 利夫
Pharmaceutical Institute Tohoku University
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平山 宗子
Pharmaceutical Institute, Tohoku University
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平山 宗子
Pharmaceutical Institute Tohoku University
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