Chiral Synthesis of Erythrina Alkaloids. I. Total Synthesis of (+)-Erysotrine via Asymmetric Diels-Alder Reaction under High Pressure

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概要

• 論文の詳細を見る

• (S)-(+)-3,4-Dimethoxyphenylalanine methyl ester (1b) was converted, in 3 steps, into (5S)-(-)-8,9-dimethoxy-1,5-dimethoxycarbonyl-2,3-dioxo-2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinoline (2b). Diels-Alder reaction of 2b with 1-methoxy-3-trimethylsilyloxybutadiene under extremely high pressure (10 kbar), followed by desilylation, gave moderate yields of erythrinan derivatives (11), which were converted, in several steps, into (+)-erysotramidine (23b) and (+)-erysotrine (4), thus accomplishing the first total synthesis of natural Erythrina alkaloids in chiral forms.

• 社団法人日本薬学会の論文
• 1993-12-15

著者

• 津田 喜典

  金沢大学

• 津田 喜典

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 細井 信造

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 細井 信造

  金沢大薬

• 津田 喜典

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 佐野 武弘

  Showa College of Pharmaceutical Sciences.

• 金子 主税

  東北大学

• 金子 主税

  Pharmaceutical Institute Medical Faculty University Of Tokyo

• 津田 喜典

  金沢大薬

• 片桐 信弥

  Pharmaceutical Institute, Tohoku University

• 佐野 武弘

  昭和薬科大学

• 佐野 武弘

  Showa Pharmaceutical Univ. Tokyo Jpn

• 佐野 武弘

  Showa College Of Pharmaceutical Sciences

• 片桐 信弥

  Health Sci. Univ. Hokkaido Hokkaido Jpn

• 片桐 信弥

  Pharmaceutical Institute Tohoku University

• Katagiri N

  Pharmaceutical Institute Tohoku University

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