Organic letters

Expeditious total syntheses of natural allenic products via aromatic ring umpolung

C Sabot, D Bérard, S Canesi

Index: Sabot, Cyrille; Berard, Didier; Canesi, Sylvain Organic Letters, 2008 , vol. 10, # 20 p. 4629 - 4632

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Citation Number: 50

Abstract

ABSTRACT Concise diastereoselective syntheses of the marine (()-panacene and terrestrial (()-desbromopanacene have been achieved in a few steps based on a concept of “aromatic ring umpolung”. The synthetic avenue to the (()-panacene involved a novel oxymercuration strategy to produce the correct configuration of the bromoallene moiety.