Chemical Conversion of Corticosteroids to 3α, 5α-Tetrahydro Derivatives. Synthesis of Allotetrahydro-11-deoxycortisol Glucuronides
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概要
- 論文の詳細を見る
A method for the conversion of 11-deoxycortisol into 3α-hydroxy-5α-compounds is described. The allotetrahydro-11-deoxycortisol monoacetates (8,14), which are key intermediates in the preparation of the 3- or 21-glucuronide of allotetrahydro-11-deoxycortisol, were the target compounds. The preparation of 5α-dihydro-11-deoxycortisol 21-acetate (4) was carried out by hydrogenation of the 3-ethoxy-3,5-diene (2), followed by acid hydrolysis. When the 21-tetrahydropyranyl ether (6) and 21-tert-butyldimethylsilyl ether (7) were treated with potassium tri-secbutylborohydride in tetrahydrofuran under mild conditions, selective reduction of the carbonyl group at C-3 took place, yielding the 3α-alcohols (9 and 10,respectively). Allotetrahydro-11-deoxycortisol 3-glucuronide (21) and allotetrahydro-11-deoxycortisol 21-glucuronide (23) were then prepared.
- 公益社団法人日本薬学会の論文
- 1985-10-25
著者
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高崎 渉
Analytical and Metabolic Research Laboratories, Sankyo Co., Ltd.,
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南原 利夫
Pharmaceutical Institute, Tohoku University
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細田 宏
Pharmaceutical Institute Tohoku University
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南原 利夫
東北大学医学部薬学科
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高崎 渉
Analytical And Metabolic Research Laboratories Sankyo Co. Ltd.
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圓山 優子
Pharmaceutical Institute Tohoku University
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三浦 裕也
Pharmaceutical Institute, Tohoku University
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頭金 正博
国立医薬品食品衛生研究所医薬安全科学部
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高崎 渉
Pharmaceutical Institute, Tohoku University
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頭金 正博
Pharmaceutical Institute, Tohoku University
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南原 利夫
Pharmaceutical Institute Tohoku University
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三浦 裕也
Pharmaceutical Institute Tohoku University
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頭金 正博
Pharmaceutical Institute Tohoku University
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