Stereochemical Studies. LIV. A Biogenetic-type Asymmetric Synthesis of optically Active Galanthamine from L-Tyrosine

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概要

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• A biogenetic-type asymmetric synthesis of optically active galanthamine ((+)-4 and (-)-4) is described. Norbelladine derivative (10), having C_2 symmetry in the aromatic moiety of C_6-C_1-N part, was prepared from L-tyrosine, and was converted to narwedinetype enone (11) by oxidation and highly specific asymmetric cyclization. Phosphorylation of phenolic hydroxyl group followed by sodium borohydride reduction afforded 14 having galanthamine skeleton. N-Methylation followed by removal of the methoxycarbonyl and phosphate moieties afforded (+)-galanthamine ((+)-4). Formal total synthesis of (-)-galanthamine ((-)-4) from L-tyrosine via enantiomeric interconversion of narwedine derivative (12) is also described.

• 社団法人日本薬学会の論文
• 1978-12-25

著者

• 山田 俊一

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 古賀 憲司

  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

• Koga Kenjiro

  Department Of Pharmaceutics Faculty Of Pharmaceutical Sciences Hokuriku University

• 清水 公博

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 富岡 清

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 清水 公博

  Faculty Of Pharmaceutical Sciences University Of Tokyo

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