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Facile synthesis of (Z)-tetracos-5-enoic acid and racemic cis-4-(2-octadecylcyclopropane-1-yl)-butanoic acid

Lookup NU author(s): Dr Geoffrey Coxon, Professor David Minnikin


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(Z)-Tetracos-5-enoic acid and racemic cis-4-(2-octadecylcyclopropane-1-yl)- butanoic acid have been prepared from 1-eicosene by a new facile route. Periodic acid cleavage of the epoxide of 1-eicosene gave nonadecanal which was condensed with 4-carboxybutyltriphenylphosphonium bromide to give predominately (Z)-tetracos-5-enoic acid. Simmons-Smith type cyclopropanation of (Z)-tetracos-5-enoic acid gave a minor proportion of racemic cis-4-(2-octadecylcyclopropane-1-yl)-butanoic acid accompanied by major amounts of its methyl ester. © 2003 Elsevier Ireland Ltd. All rights reserved.

Publication metadata

Author(s): Coxon GD, Douglas JD, Minnikin DE

Publication type: Article

Publication status: Published

Journal: Chemistry and Physics of Lipids

Year: 2003

Volume: 126

Issue: 1

Pages: 49-53

ISSN (print): 0009-3084

ISSN (electronic): 1873-2941

Publisher: Elsevier Ireland


DOI: 10.1016/S0009-3084(03)00092-6

PubMed id: 14580710


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