Amino Acids and Peptides. XIII. A New Approach to the Biogenetictype, Asymmetric Synthesis of Indole and Isoquinoline Alkaloids by 1,3-Transfer of Asymmetry

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概要

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• A new approach to the synthesis of optically active indole and isoquinoline alkaloids is described. The key reactions are : (i) the biogenetic-type, asymmetric Pictet-Spengler reaction of optically active α-amino acids (I) with aldehydes (II) (1,3-asymmetric induction), and (ii) the elimination of the chiral center derived from α-amino acids (1,3-transfer of asymmetry), shown in Chart 1. To achieve (ii), laboratory simulation of decarboxylative processes of α-amino acids was investigated by oxidative and reductive methods. The former did not give any fruitful results, as shown in Table I. However, the reduction of α-amino nitriles, easily prepared from α-amino acids, by means of sodium borohydride gave the satisfactory result, as shown in Table II. By this new method, two simple indole alkaloids, (S)-(-)-tetrahydroharman (XXIV) and (S)-(-)-1,2,3,4,6,7,12,12b-octahydroindolo [2,3-a] quinolizine (XXIX) could be obtained from L-tryptophan in a satisfactory manner.

• 公益社団法人日本薬学会の論文
• 1974-11-25

著者

• 山田 俊一

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 塩入 孝之

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 山田 俊一

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 塩入 孝之

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 岡村 久也

  Kyorin Chemical Laboratory, Kyorin Pharmuceutical Co., Ltd.

• 倉本 正志

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 秋元 浩

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 岡村 久也

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 勇伊 実

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 川瀬 雅子

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 秋元 浩

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 川瀬 雅子

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 勇伊 実

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 倉本 正志

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 岡村 久也

  Kyorin Chemical Laboratory Kyorin Pharmuceutical Co. Ltd.

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