Synthesis of Epimeric 2-d_1-5β-Pregnane-3,11,20-triones
スポンサーリンク
概要
- 論文の詳細を見る
In order to clarify the stereochemistry of hydrogen loss from the C-2 position during microbial transformation of 5β-pregnane-3,11,20-trione into the Δ^1-unsaturated compound, the stereospecific synthesis of epimeric C-2 deuterated substrates has been carried out. A key intermediate, 5β-pregn-2-ene-11α, 20β-diol diacetate, was obtained from the readily available 11α-hydroxyprogesterone through two synthetic routes. The trans-diaxial opening of the 2β, 3β-epoxide with lithium aluminum deuteride provided the 2α-d_1-3β-ol. Deuterioboration of the Δ^2-olefin and subsequent oxidation of the organoborane afforded the 2α-d_1-3β-ol. On oxidation with chromium trioxide-pyridine complex, the epimeric 2-d_1-5β-pregnane-3β, 11α, 20β-triols were converted to the desired 2-d_1-5β-pregnane-3,11,20-triones.
- 公益社団法人日本薬学会の論文
- 1979-08-25
著者
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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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日野 好弘
Pharmaceutical Institute, Tohoku University
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砂川 正幸
Pharmaceutical Institute, Tohoku University
-
砂川 正幸
Pharmaceutical Institute Tohoku University
-
日野 好弘
Pharmaceutical Institute Tohoku University
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