The Journal of Organic Chemistry

Chiral total synthesis of indole alkaloids of the Aspidosperma and Hunteria types

M Node, H Nagasawa, K Fuji

Index: Node, Manabu; Nagasawa, Hideko; Fuji, Kaoru Journal of Organic Chemistry, 1990 ,  vol. 55,  # 2  p. 517 - 521

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Citation Number: 98

Abstract

Expeditious enantioselective syntheses of (+)-quebrachamine (6),(-)-aspidospermidine (7),(+)-demethoxyaspidospermine (8), and (-)-eburnamonine (9) were accomplished starting from (S)-lactone 1. The syntheses also complete formal, total syntheses of 12 other indole alkaloids of the Aspidosperma and Hunteria types. The key step in the synthesis of (+)- quebrachamine (6) was the Pictet-Spengler condensation of chiral Cg unit 10, derived ...