A-Substituted 5β-Steroids. III. Synthesis of 2-Oxo- 5β-steroids and Their Derivatives
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概要
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The synthesis of 2-oxo- 5β-steroids (5β-cholestan-2-one and methyl 2-oxocholanate) and their derivatives have been described. Both oxo-steroids were prepared from 2β-acetoxy-3-oxo- 5β-ste-roids according to the following synthetic pathways: (a) condensation with ethylmercaptan to diethylmercaptol, desulfurization, hydrolysis and oxidation, (b) condensation with ethylmercaptan to diethylmercaptol, hydrolysis to hydroxy-ethylmercaptol, desulfurization and oxidation, and (c) isomerisation to 3α-acetoxy-2-oxo derivative and deacetylation with zinc powder to 2-oxo derivative. In these pathways, it was found that method (b) gave the best yield. On the other hand, desulfurization of the hydroxy-mercaptols with one-half the weight of Raney nickel used for that of method (b) gave 2β-hydroxy- 3β-ethylthio derivatives as intermediates. Reductive cleavage of these hydroxy-ethylthio derivatives with Raney nickel produced 2β-hydroxy- 5β-steroids in good yields. In the halogenation of these 2-oxo derivatives, the products were 1β-halo-2-oxo- 5β-sterodis, not 1α- or 3-halo isomers.
- 公益社団法人 日本化学会の論文
著者
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Satoh Yasuo
Department Of Anesthesiology Toho University Sakura Medical Center
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Horiuchi Akira
Department Of Chemistry Rikkyo (st. Paul's) University
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Horiuchi Akira
Department of Chemistry, College of Science, St. Paul's University (Rikkyo Daigaku)
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Hagitani Akira
Department of Chemistry, St. Paul's (Rikkyo) University
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Hagitani Akira
Department of Chemistry, College of Science, Rikkyo (St. Paul's) University
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Satoh Yasuo
Department of Chemistry, College of Science, St. Paul's University (Rikkyo Daigaku)
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