Highly stereoselective total syntheses of (+)-allopumiliotoxins 267A and 339A via intramolecular nickel (II)/chromium (II)-mediated cyclization

S Aoyagi, TC Wang, C Kibayashi

Index: Aoyagi, Sakae; Wang, Tzu-Chueh; Kibayashi, Chihiro Journal of the American Chemical Society, 1993 , vol. 115, # 24 p. 11393 - 11409

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Citation Number: 70

Abstract

Abstract: Remarkably high regio-and stereoselective approaches for the syntheses of dendrobatid alkaloids (+)-allopumiliotoxin 267A and 339A have been developed. As a model study for the syntheses of these alkaloids, we initially undertook intramolecular chromium (11)-mediated cyclization of the racemic N-(iodoalkeny1) piperidine 8, which smoothly proceeded by treatment with CrC12 (5 equiv) and catalytic NiC12 (2.5 mol 9%) ...

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