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

G.D. Coxon, J.D. Douglas, D.E. Minnikin

Research output: Contribution to journalArticle

3 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)49-53
Number of pages5
JournalChemistry and Physics of Lipids
Volume126
Issue number1
DOIs
Publication statusPublished - 2003

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Keywords

  • fatty acids
  • alkene stereochemistry
  • mycolic acids
  • Wittig reaction
  • cyclopropane rings

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