Amino Acids and Peptides. XVIII. A Biogenetic-type, Asymmetric Synthesis of (S)-Reticuline 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 (S)-reticuline (I) was accomplished by means of the biogenetic-type, asymmetric Pictet-Spengler reaction of 3-(3-hydroxy-4-benzyloxyphenyl)-L-alanine methyl ester hydrochloride (XXIII) with sodium 3-benzyloxy-4-methoxy-phenylglycidate (XXIV) (1,3-asymmetric induction) and the elimination of the chiral center derived from XXIII (1,3-transfer of asymmetry), the latter of which was achieved by conversion of the cyclized α-amino acid methyl ester (XXVa) to the N-benzyl α-amino nitrile (XXVIII), followed by reductive decyanization with sodium borohydride. The position of the benzyl group of XXIII which was prepared from L-dopa by monobenzylation was proved by the alternate synthesis of XXIII starting from L-tyrosine. By this success, morphinanedienone, aporphine and protoberberine alkaloids, (-)-pallidine (XXXII), (+)-isoboldine (XXXIII), (-)-coreximine (XXXIV), and (-)-scoulerine (XXXV) are formally to have been synthesized from L-dopa.

• 公益社団法人日本薬学会の論文
• 1975-05-25

著者

• 近田 美紀彦

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 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

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

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