Cyclic Allyl Carbamates in Stereoselective syn SE′ Processes: Synthetic Approach to Sarcodictyins and Eleutherobin

S Dhulut, A Bourin, MI Lannou, E Fleury…

Index: Dhulut, Sylvie; Bourin, Arnaud; Lannou, Marie-Isabelle; Fleury, Etienne; Lensen, Nathalie; Chelain, Evelyne; Pancrazi, Ange; Ardisson, Janick; Fahy, Jacques European Journal of Organic Chemistry, 2007 , # 31 p. 5235 - 5243

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Citation Number: 3

Abstract

Abstract Our synthetic approach of marine diterpenoids sarcodictyins A and B and eleutherobin relies on the one-step attachment of a C5–C9 side chain at the C10 position. The C1, C10 cis-disubstituted cyclohexene derivative is obtained in 86% yield with total stereoselectivity. The reaction is based on a syn SE′ process involving a cyclic (Z)-allyl diisopropylcarbamate.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, ...