Synthetic Approaches to Fumitremorgins. III. : Synthesis of Optically Active Pentacyclic Ring Systems, and Their Oxidation at Ring C

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概要

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• Pictet-Spengler reaction of L-tryptophan methyl ester (9) and 6-methoxy-L-tryptophan methyl ester (40) with isovaleraldehyde (10) in methylene chloride in the presence of trifluoroacetic acid gave the cis-tetrahydro-β-carboline (11,41) as the major isomer. The condensation of 11 and 41 with N-benzyloxycarbonyl-L-proline followed by deprotection gave the cis-cis-pentacycles (27,44) which contain the parent ring system of fumitremorgins. The trans-cis(28), the cis-trans (29,30) and the trans-trans (31) pentacycles were similarly prepared. Isopentylation of 27 and 44 gave the N_a-isopentyl derivatives (52,53) accompanied with epimerization at the 12-position. Oxidation of 52 and 53 with dichlorodicyano-p-benzoquinone (DDQ) gave the 12,13-dehydro derivatives (54,55) which provided demethoxy-13-epi-tetrahydrofumitremorgin B (57) and 17-bromo-13-epi-tetrahydro-fumitremorgin B (58) by N-bromosuccinimide (NBS)-oxidation in aqueous dimethoxyethane. Debromination of 58 gave 13-epi-tetrahydrofumitremorgin B (59).

• 社団法人日本薬学会の論文
• 1989-01-25

著者

• 中川 昌子

  Faculty of Pharmaceutical Sciences, Chiba University

• 日野 亨

  Faculty of Pharmaceutical Sciences, Chiba University

• 中川 昌子

  千葉大薬

• 川手 智彦

  千葉大薬

• 日野 亨

  千葉大 薬

• 川手 智彦

  Faculty of Pharmaceutical Sciences, Chiba University

• 福島 浩

  Faculty of Pharmaceutical Sciences, Chiba University

• 本宮 光弥

  Faculty of Pharmaceutical Sciences, Chiba University

• [ウネ] 輝昭

  Faculty of Pharmaceutical Sciences, Chiba University

• 古田土 真一

  Faculty of Pharmaceutical Sciences, Chiba University

• 谷口 幹雄

  Faculty of Pharmaceutical Sciences, Chiba University

• 古田土 真一

  Faculty Of Pharmaceutical Sciences Chiba University

• 谷口 幹雄

  Faculty Of Pharmaceutical Sciences Chiba University

• 中川 昌子

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 福島 浩

  Faculty Of Pharmaceutical Sciences Chiba University

• 中川 昌子

  千葉大 薬

• 本宮 光弥

  Faculty Of Pharmaceutical Sciences Chiba University

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