organic letters

Studies of new indole alkaloid coupling methods for the synthesis of haplophytine

PD Rege, Y Tian, EJ Corey

Index: Rege, Pankaj D.; Tian, Yuan; Corey Organic Letters, 2006 , vol. 8, # 14 p. 3117 - 3120

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Citation Number: 21

Abstract

Haplophytine (1) is a potent insecticidal alkaloid isolated from the Central American plant Haplophyton cimicidum that consists of two alkaloidal subunits joined together in a highly unusual way. 1-4 Upon exposure to HBr, haplophytine undergoes a unique 1,2-cationic shift to generate the rearranged iminium bromide structure 2, which clearly contains two indole moieties that are the most likely building blocks for the biosynthetic pathway. The more complex of these ...