New Synthetic Routes to (±)-Perhydrohistrionicotoxin. Stereoselective Synthesis of (6S^*, 7S^*, 8S^*)-7-Butyl-8-hydroxy-1-azaspiro [5.5]-undecan-2-one and Its (6R^*)-Isomer

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概要

• 論文の詳細を見る

• A highly stereoselective synthesis of (6S^*, 7S^*, 8S^*)-7-butyl-8-hydroxy-1-azaspiro [5.5]-undecan-2-one (6), a key intermediate for (±)-perhydrohistrionicotoxin synthesis, from the Diels-Alder cycloadduct of 1,3-bis (trimethylsiloxy)-2-methyl-1,3-butadiene (15) and ethyl 3-acetoxy-1-cyclohexene-1-carboxylate is described. This key intermediate and its stereoisomer, (6R^*, 7S^*, 8S^*)-7-butyl-8-hydroxy-1-azaspiro [5.5] undecan-2-one (7), were stereoselectively synthesized by means of a conjugate addition reaction using 1-(3-tert-butyldimethylsiloxy-1-cyclohexen-1-yl)-ethanone and BuCu・AlCl_3 as the key step.

• 公益社団法人日本薬学会の論文
• 1982-08-25

著者

• 犬伏 康夫

  Faculty of Pharmaceutical Sciences, Kyoto University

• 井深 俊郎

  Faculty of Pharmaceutical Sciences, Kyoto University

• 南方 宏之

  (財)サントリー生有研

• 南方 宏之

  Faculty Of Pharmaceutical Sciences Kyoto University

• 多賀 徹

  Faculty of Pharmaceutical Sciences, Kyoto University

• 多賀 徹

  京大・薬

• 井深 俊郎

  Faculty Of Pharmaceutical Sciences Kyoto University

• 犬伏 康夫

  Faculty Of Pharmaceutical Sciences Kyoto University

• 南方 宏之

  財団法人サントリー生物有機科学研究所

• 多賀 徹

  京大・院薬・薬品分子構造

• 三井 義則

  Faculty of Pharmaceutical Sciences, Kyoto University

• 林 憲司

  Faculty of Pharmaceutical Sciences, Kyoto University

• 多賀 徹

  Faculty Of Pharmaceutical Sciences Kyoto University

• 三井 義則

  Faculty Of Pharmaceutical Sciences Kyoto University

• 南方 宏之

  サントリー生物有機科学研

• 林 憲司

  Faculty Of Pharmaceutical Sciences Kyoto University

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