Synthesis of (-)-ilimaquinone via a radical decarboxylation and quinone addition reaction

T Ling, E Poupon, EJ Rueden, EA Theodorakis

Index: Ling, Taotao; Poupon, Erwan; Rueden, Erik J; Theodorakis, Emmanuel A Organic letters, 2002 , vol. 4, # 5 p. 819 - 822

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Citation Number: 33

Abstract

A stereoselective synthesis of (-)-ilimaquinone (4) is presented. The synthetic strategy is based on a novel radical decarboxylation and quinone addition methodology that produces quinone 7 from reaction of thiohydroxamic acid derivative 8 with benzoquinone (9). Final functionalization of 7 to ilimaquinone (4) is achieved by exploring the electronic effects of the residual thiopyridyl group.