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Communication | Regular issue | Vol 27, No. 5, 1988, pp.1131-1134
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4473
A Simple Preparation of (R)-(+)-β-(3,4,5-Trimethoxybenzyl)-butanolide, and Its Use in tne Total Syntheses of Naturally Occurring Dibenzylbutanolide Lignans

Khalid Lalami, Robert Dhal, and Eric Brown

*Laboratorie de Synthèse, Faculté des Sciences, Route de Laval, BP 535, 72017 Le Mans Cedex, France

Abstract

Resolution of methyl α-(3,4,5-trimethoxybeneyl)hemisuccinate by means of (-)-ephedrine, followed by calcium borohydride reduction, afforded (R)-(+)-β-(3,4,5-triméthoxybenzyl)butanolide. This lactone was used as s starting material for the optically active syntheses of 8 recently discovered lignans belonging to, or deriving from the α,β-dibenzylbutanolide series, such as isoyatein, cubebinone and dihydroclusin.