Organic Letters 2005-10-27

Synthesis of farnesol isomers via a modified Wittig procedure.

José S Yu, Troy S Kleckley, David F Wiemer

Index: Org. Lett. 7 , 4803-4806, (2005)

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Abstract

[structure: see text] The four olefin stereoisomers of farnesol have been synthesized from readily available nerylacetone or commercial geranylacetone. A new variation on the use of beta-oxido ylides favored the (2Z)-stereoisomers, whereas the (2E)-isomers were obtained through a classical Horner-Wadsworth-Emmons condensation with triethyl phosphonoacetate and reduction of the resulting ester.