Electroorganic chemistry. 113. Synthesis of (+)-and (-)-N-methylpseudoconhydrine from L-lysine using anodic oxidation as the key reaction

T Shono, Y Matsumura, O Onomura…

Index: Shono; Matsumura; Onomura; Sato Journal of Organic Chemistry, 1988 , vol. 53, # 17 p. 4118 - 4121

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Citation Number: 55

Abstract

Compound 7, a key intermediate for the synthesis of (+)-1, was obtained from 4 in 71% yield by similar procedures. The hydroxyl group of 7 was easily removed by reducing 7 with NaBH4 and a stereoisomeric mixture of 8a and 8b was obtained in 69% yield. The stereochemistry of the 5-acetoxyl group of 7 was unknown, but the stereochemistry of 8 was found to mainly be trans (9: l). After each stereoisomer was separated by column ...