35 L-Tryptophan及びL-Dopaより光学活性Indole AlkaloidならびにIsoquinoline Alkaloidの生合成的不斉合成

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概要

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• Some α-amino acids(I)(L-tryptophan and L-Dopa) were subjected to the Pictet-Spengler reaction with aldehydes(II) according to the biosynthetic route. From the resultant condensation products (III) was eliminated the C_1-unit derived from the α-amino acids to give optically active compounds(IV). Using this biogenetically patterned 1,3-transfer of asymmetry, S(-)-tetrahydroharman(XVIIb) and S(-)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine(XX) were synthesized from L-tryptophan. S(+)-Laudanosine(XXVIa) was also prepared from L-Dopa. The key steps of the 1,3-transfer of asymmetry are the Pictet-Spengler reaction, α-aminonitrile formation, followed by the reductive decyanization with sodium borohydride. Results of model reactions for the reductive decyanization are shown in the Table.

• 天然有機化合物討論会の論文
• 1972-10-01

著者

• 塩入 孝之

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 岡村 久也

  Kyorin Chemical Laboratory, Kyorin Pharmuceutical Co., Ltd.

• 山田 俊一

  東大薬

• 塩入 孝之

  東大薬

• 秋元 浩

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 秋元 浩

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 秋元 浩

  東大薬

• 岡村 久也

  東大薬

• 近田 美紀彦

  東大薬

• 岡村 久也

  Kyorin Chemical Laboratory Kyorin Pharmuceutical Co. Ltd.

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