Synthesis of farnesol isomers via a modified Wittig procedure

José S Yu; Troy S Kleckley; David F Wiemer

doi:10.1021/ol0513239

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Synthesis of farnesol isomers via a modified Wittig procedure

Journal article

Peer reviewed

Synthesis of farnesol isomers via a modified Wittig procedure

José S Yu, Troy S Kleckley and David F Wiemer

Organic letters, Vol.7(22), pp.4803-4806

10/27/2005

DOI: 10.1021/ol0513239

PMID: 16235893

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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.

Chemistry, Organic - methods

Molecular Structure

Stereoisomerism

Farnesol - chemical synthesis

Farnesol - chemistry

Details

Title: Subtitle: Synthesis of farnesol isomers via a modified Wittig procedure
Creators: José S Yu - Department of Chemistry, University of Iowa, Iowa City, 52242, USA
Troy S Kleckley
David F Wiemer
Resource Type: Journal article
Publication Details: Organic letters, Vol.7(22), pp.4803-4806
Publisher: United States
DOI: 10.1021/ol0513239
PMID: 16235893
ISSN: 1523-7060
eISSN: 1523-7052
Language: English
Date published: 10/27/2005
Academic Unit: Neuroscience and Pharmacology; Chemistry
Record Identifier: 9983985812002771

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