Stereochemistry of Methyl 2-Benzyl-3-methoxycarbonyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido [3,4-b] indole-1-propionate

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概要

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• The Pictet-Spengler reaction of N_a-methyl-N_b-benzyltryptophan methyl ester hydrochloride (4a) with methyl 3-formylpropionate was carried out in 50% aqueous MeOH under reflux to afford methyl trans-2-benzyl-3-methoxycarbonyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido [3,4-b] indole-1-propionate (3a) as a major product and trans-2-benzyl-3-methoxycarbonyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido [3,4-b] indole-1-propionic acid (5a) as a minor product. In earlier work, the stereochemistry of the major product 3a had been erroneously assigned as 1,3-cis (3b), while the minor product 5a had been incorrectly assigned as the 1,3-trans compound 3a. Compound 3b was not formed in this reaction. The stereochemistry of the major product (3a) was confirmed by X-ray crystallographic analysis in the present work.

• 1984-02-25

著者

• 山口 啓一

  Faculty of Pharmaceutical Sciences, Chiba University

• 米田 直人

  Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.

• 菰田 泰夫

  Institute for Medical and Dental Engineering, Tokyo Medical and Dental University

• 米田 直人

  Research Laboratory Of Applied Biochemistry Tanabe Seiyaku Co. Ltd.

• 清水 正人

  Research Institute For Medical And Dental Engineering Tokyo Medical And Dental University

• 清水 正人

  Institute For Medical And Dental Engineering Tokyo Medical And Dental University

• 中嶋 暉躬

  Institute of Pharmaceutical Sciences, School of Medicine, Hiroshima University

• 中嶋 暉躬

  Suntory Institute For Bioorganic Research

• 石川 正幸

  Research Institute For Medical And Dental Engineering Tokyo Medical And Dental University

• 石川 正幸

  Institute For Medical And Dental Engineering Tokyo Medical And Dental University

• 菰田 泰夫

  医歯大・医用研・化学

• 菰田 泰夫

  Institute For Medical And Dental Engineering Tokyo Medical And Detal University

• 山口 啓一

  Faculty Of Pharmaceutical Sciences Chiba University

• 菰田 泰夫

  Institute For Medical And Dental Engineering Tokyo Medical And Dental University

• 米田 直人

  Research Laboratory of Applied Biochemistry

• 米田 直人

  Research Laboratory of Applied Biochemistry Tanabe Seiyaku Co., Ltd.

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