Chemical Synthesis of 11-Deoxycortisol Metabolites

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概要

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• The synthesis of the 3-glucuronides of 11-deoxycortisol metabolites is described. 3α, 17α, 20α-Trihydroxy-5β-pregnan-21-oic acid 3-glucuronide (13) and its 20β-epimer (14) were prepared starting from 5β-dihydro-11-deoxycortisol (1). The 20-acetoxy-21-oic acid methyl esters (7,8) were the key intermediates. Oxidation of 1 with cupric acetate followed by the intramolecular Cannizzaro reaction gave the 20-epimeric 20-hydroxy-21-acids (5,6), which, on methylation with diazomethane followed by acetylation, were converted into the acetate-methyl esters (3,4). Reduction of the carbonyl group at C-3 in 3 and 4 with sodium borohydride gave the desired intermediates. Introduction of the glucuronyl residue at the C-3 position was carried out by means of the Koenigs-Knorr reaction. 20-Epimeric 5β-pregnane-3α, 17α, 20,21-tetrol 3-glucuronides (26,27) were also prepared.

• 1985-03-25

著者

• 南原 利夫

  Pharmaceutical Institute, Tohoku University

• 細田 宏

  Pharmaceutical Institute Tohoku University

• 塩谷 宏明

  Pharmaceutical Institute, Tohoku University

• 南原 利夫

  東北大学医学部薬学科

• 横浜 廣光

  Pharmaceutical Institute, Tohoku University

• 横浜 廣光

  Pharmaceutical Institute Tohoku University

• 南原 利夫

  Pharmaceutical Institute Tohoku University

• 塩谷 宏明

  Pharmaceutical Institute Tohoku University

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