Studies on Digitalis Glycosides. XXXIV. Transformation of Gitoxigenin to Digitoxigenin 3-Acetate

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概要

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• Treatment of 16β, 17β-epoxy-17α-digitoxigenin 3-acetate (V), which is readily available from gitoxigenin (Ib), with dilute alkali in absolute ethanol gave 16,17-dehydro-21R-ethoxydigitoxigenin 3-acetate (VIII) and 21S-epimer (IX). Catalytic hydrogenation of VIII and IX gave stereospecifically 21R-ethoxydigitoxigenin 3-acetate (X) and 21S-ethoxy-17α-digitoxigenin 3-acetate (XI), respectively. Further reduction of X and XI with NaBH_4 effectively eliminated ethoxy group to afford digitoxigenin 3-acetate (IVb) and 17α-epimer (III), respectively. By the sequence of these reactions, chemical transformation of gitoxigenin (Ib) to digitoxigenin 3-acetate (IVb) was achieved in fair yield.

• 公益社団法人日本薬学会の論文
• 1977-09-25

著者

• 豊岡 康平

  Faculty of Pharmaceutical Sciences, University of Tokushima

• 橋本 敏弘

  Faculty of Pharmaceutical Sciences, Tokushima Bunri University

• 佐藤 大助

  Faculty Of Pharmaceutical Sciences Tokushima Bunri University

• 芝原 弘子

  Faculty of Pharmaceutical Sciences, Tokushima Bunri University

• 豊岡 康平

  Faculty Of Pharmaceutical Sciences University Of Tokushima

• 橋本 敏弘

  徳島文理大学薬学部

• 山原 好信

  Faculty of Pharmaceutical Science Tokushima Bunri University

• 芝原 弘子

  Faculty Of Pharmaceutical Sciences Tokushima Bunri University

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