Synthesis of Cortoic Acid 3-Glucuronides
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概要
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The synthesis of the 3-glucuronides of cortoic acids, metabolites of cortisol, is described. 20α-Cortolonic acid 3-glucuronide (11) and its 20β-epimer (12) were prepared starting from tetrahydrocortisone (1). The cortolonic acid 20-acetate methyl esters (7,8) were the key intermediates. The 20-oxo-21-aldehyde (2) obtained from 1 by oxidation with cupric acetate was derivatized into 20-epimeric methyl cortolonates (3). When 3 was treated with tert-butyldimethylsilyl chloride and imidazole in dimethylformamide-pyridine, selective silylation of the hydroxyl group at C-3 took place. Subsequent acetylation with acetic anhydride in pyridine gave the separable 20-acetates (5,6), which, on removal of the silyl group at C-3 with sulfuric acid, were converted into the desired intermediates. Introduction of the glucuronyl residue into the C-3 position was carried out by means of the Koenigs-Knorr reaction. The cortolic acid 3-glucuronides (21,22) were synthesized from 5β-dihydrocortisol (13).
- 公益社団法人日本薬学会の論文
- 1984-04-25
著者
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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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横浜 廣光
Pharmaceutical Institute, Tohoku University
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横浜 廣光
Pharmaceutical Institute Tohoku University
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南原 利夫
Pharmaceutical Institute Tohoku University
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