Amino Acids and Peptides. XVII. A Biogenetic-type, Asymmetric Synthesis of (S)-Laudanosine from L-3-(3,4-Dihydroxyphenyl) alanine by 1,3-Transfer of Asymmetry

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概要

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• The asymmetric synthesis of a representative benzylisoquinoline alkaloid, (S)-(+)-laudanosine (III) was accomplished by means of the biogenetic-type, asymmetric Pictet-Spengler reaction of L-3-(3,4-dihydroxyphenyl) alanine methyl ester hydrochloride (IV) with sodium (3,4-dimethoxyphenyl) glycidate (V) (1,3-asymmetric induction) and the elimination of the chiral center derived from IV (1,3-transfer of asymmetry). The latter was conveniently achieved by conversion of the cyclized α-amino acid methyl ester (VIa) to the N-benzyl α-amino nitrile (XIII), followed by reductive decyanization with sodium borohydride.

• 公益社団法人日本薬学会の論文
• 1975-05-25

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

• 近田 美紀彦

  The Organic Chemistry Research Laboratory of Tanabe Seiyaku Co. Ltd.

関連論文

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