Synthesis of the Imidazo [1,2-a] indole-spirolactone Ring System by Oxidative Double Cyclization. A Synthetic Approach to Tryptoquivalines

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概要

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• Imidazo [1,2-a] indole-spirolactone 13,the principal ring system of tryptoquivalines, was successfully synthesized by a new method via oxidative double cyclization of 1-(N-alkoxy-carbonylalanyl)-3-indolepropionic acids (5) with N-bromosuccinimide, which were synthesized by acylation of benzyl 3-indolepropionate (10) with N-alkoxycarbonyl alanine p-nitrophenyl ester (12). The use of KF, 18-crown-6 and (iso-Pr)_2NEt in acetonitrile lead to high yields of benzyl 1-(N-methoxycarbonyl-α-methylalanyl)-3-indolepropionates (4). The removal of the protecting group of 13c provided 2. The mechanisms of these reactions are discussed.

• 社団法人日本薬学会の論文
• 1984-04-25

著者

• 中川 昌子

  Faculty of Pharmaceutical Sciences, Chiba University

• 日野 亨

  Faculty of Pharmaceutical Sciences, Chiba University

• 山口 啓一

  Faculty of Pharmaceutical Sciences, Chiba University

• 中川 昌子

  千葉大薬

• 日野 亨

  千葉大 薬

• 袖岡 幹子

  Faculty of Pharmaceutidal Sciences, Chiba University

• 中川 昌子

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 中川 昌子

  千葉大 薬

• 袖岡 幹子

  Faculty Of Pharmaceutidal Sciences Chiba University

• 山口 啓一

  Faculty Of Pharmaceutical Sciences Chiba University

• 山口 啓一

  Faculty Of Pharmaceutidal Sciences Chiba University

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