1-(1-Pyrrolin-2-yl)-β-carbolines. Synthesis of Eudistomins H, I, and P

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概要

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• Three marine β-carboline alkaloids, eudistomin H, I, and P (5,4,and 6), were synthesized. The Bischler-Napieralski reaction of N-(N-benzyloxycarbonylprolyl)tryptamine (11) gave the 3,4-dihydro-β-carboline (12), which was converted to eudistomin I (5) via 13 on deprotection and dehydrogenation. Compound 13 was obtained directly from N-(N-tert-butoxycarbonylprolyl)tryptamine (17) by means of the Bischler-Napieralski reaction with polyphosphoric ester-dichloroethane. The bromination of 5 with N-bromosuccinimide (NBS)-acetic acid gave eudistomin H (4). Bromination of the 5-methoxypyrrolo[2,3-b]indole (21) obtained from the 5-hydroxytryptamine (18) gave the 6-bromo derivative (22) which afforded 6-bromo-5-methoxytryptamine (25) on alkaline hydrolysis. The Bischler-Napieralski reaction of the 6-bromo-5-methoxy-N-prolyltryptamine (27) gave the 1-pyrrolinyl-3,4-dihydro-β-carboline (29). Dehydrogenation of 29 with NBS followed by demethylation with boron tribromide provided eudistomin P (6) via 30.

• 社団法人日本薬学会の論文
• 1989-10-25

著者

• 中川 昌子

  Faculty of Pharmaceutical Sciences, Chiba University

• 日野 亨

  Faculty of Pharmaceutical Sciences, Chiba University

• 関 宏子

  The Chemical Analysis Center Chiba University

• 中川 昌子

  千葉大薬

• 日野 亨

  千葉大 薬

• 原 りつ子

  The Chemical Analysis Center

• 倉持 忠雄

  The Chemical Analysis Center

• 頼 梓平

  Faculty of Pharmaceutial Sciences

• 中川 昌子

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 中川 昌子

  千葉大 薬

• 倉持 忠雄

  The Chemical Analysis Center:chiba University

• 原 りつ子

  The Chemical Analysis Center:chiba University

• 頼 梓平

  Faculty Of Pharmaceutial Sciences:chiba University

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