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

Coxon, G.D. and Douglas, J.D. and Minnikin, D.E. (2003) Facile synthesis of (Z)-tetracos-5-enoic acid and racemic cis-4-(2-octadecylcyclopropane-1-yl)-butanoic acid. Chemistry and Physics of Lipids, 126 (1). pp. 49-53. ISSN 0009-3084

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Official URL: https://doi.org/10.1016/S0009-3084(03)00092-6

Abstract

(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.

Author(s):	Coxon, G.D. ORCID: https://orcid.org/0000-0002-3541-5236, Douglas, J.D. and Minnikin, D.E.
Item type:	Article
ID code:	37922
Keywords:	fatty acids, alkene stereochemistry, mycolic acids, Wittig reaction, cyclopropane rings, Pharmacy and materia medica, Biochemistry, Cell Biology, Organic Chemistry, Molecular Biology
Subjects:	Medicine > Pharmacy and materia medica
Department:	Faculty of Science > Strathclyde Institute of Pharmacy and Biomedical Sciences
Depositing user:	Pure Administrator
Date deposited:	27 Feb 2012 14:16
Last modified:	15 Jan 2020 20:51
URI:	https://strathprints.strath.ac.uk/id/eprint/37922
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