Stereochemical Studies. LIII. An Asymmetric Synthesis of (3S 15S 20R)-Yohimbone from L-Tryptophan by 1,3-Transfer of Asymmetry

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概要

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• The asymmetric synthesis of (3S 15S 20R)-(-)-yohimbone (III) was accomplished. The key reactions in the process are : (i) the asymmetric Pictet-Spengler reaction of L-tryptophan (IV) with sodium 3-(m-methoxyphenyl) glycidate (V) (1,3-asymmetric induction), and (ii) the elimination of the chiral center derived from IV (1,3-transfer of asymmetry). The latter was conveniently achieved by converting the cyclic α-amino acid amide (XIIIa) to the pentacyclic α-amino nitrile (XIV), followed by reductive decyanization with sodium borohydride. Thus, the indole alkaloids, natural yohimbol (XX) and natural corynantheine (XXI), may be synthesized from L-tryptophan.

• 社団法人日本薬学会の論文
• 1978-08-25

著者

• 山田 俊一

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 山田 俊一

  東京大学

• 山田 俊一

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 岡村 久也

  Kyorin Chemical Laboratory, Kyorin Pharmuceutical Co., Ltd.

• 岡村 久也

  Kyorin Chemical Laboratory Kyorin Pharmuceutical Co. Ltd.

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