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
Full text not available in this repository. (Request a copy from the Strathclyde author)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.
| Item type: | Article |
|---|---|
| ID code: | 37922 |
| Keywords: | fatty acids, alkene stereochemistry, mycolic acids, Wittig reaction, cyclopropane rings, Pharmacy and materia medica |
| Subjects: | Medicine > Pharmacy and materia medica |
| Department: | Faculty of Science > Strathclyde Institute of Pharmacy and Biomedical Sciences |
| Related URLs: | |
| Depositing user: | Pure Administrator |
| Date Deposited: | 27 Feb 2012 14:16 |
| Last modified: | 12 Mar 2012 11:48 |
| URI: | http://strathprints.strath.ac.uk/id/eprint/37922 |
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