A highly stereoselective and iterative approach to isoprenoid chains: Synthesis of homogeraniol, homofarnesol, and homogeranylgeraniol

P Kocienski, S Wadman, K Cooper

Index: Kocienski, Philip; Wadman, Sjoerd; Cooper, Kelvin Journal of Organic Chemistry, 1989 , vol. 54, # 5 p. 1215 - 1217

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Citation Number: 41

Abstract

We recently described a highly stereoselective synthesis of trisubstituted homoallylic alcohols based on the Ni-(0)-catalyzed coupling of Grignard reagents with 5-alkyl-2, 3- dihydrofurans' first reported by Wenkert and coworkers.* The reaction is easy to do on a substantial scale and generally gives good yields. In this note we show how the procedure can be applied in an iterative sense to the synthesis of the isoprenoids homogeraniol (5), ...