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.
LanguageEnglish
Pages49-53
Number of pages5
JournalChemistry and Physics of Lipids
Volume126
Issue number1
DOIs
Publication statusPublished - 2003

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Periodic Acid
Acids
Epoxy Compounds
Bromides
Esters
4-(2-octadecylcyclopropane-1-yl)butanoic acid

Keywords

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

Cite this

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title = "Facile synthesis of (Z)-tetracos-5-enoic acid and racemic cis-4-(2-octadecylcyclopropane-1-yl)-butanoic acid",
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.",
keywords = "fatty acids, alkene stereochemistry, mycolic acids, Wittig reaction, cyclopropane rings",
author = "G.D. Coxon and J.D. Douglas and D.E. Minnikin",
year = "2003",
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language = "English",
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journal = "Chemistry and Physics of Lipids",
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number = "1",

}

Facile synthesis of (Z)-tetracos-5-enoic acid and racemic cis-4-(2-octadecylcyclopropane-1-yl)-butanoic acid. / Coxon, G.D.; Douglas, J.D.; Minnikin, D.E.

In: Chemistry and Physics of Lipids, Vol. 126, No. 1, 2003, p. 49-53.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Facile synthesis of (Z)-tetracos-5-enoic acid and racemic cis-4-(2-octadecylcyclopropane-1-yl)-butanoic acid

AU - Coxon, G.D.

AU - Douglas, J.D.

AU - Minnikin, D.E.

PY - 2003

Y1 - 2003

N2 - (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.

AB - (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.

KW - fatty acids

KW - alkene stereochemistry

KW - mycolic acids

KW - Wittig reaction

KW - cyclopropane rings

U2 - 10.1016/S0009-3084(03)00092-6

DO - 10.1016/S0009-3084(03)00092-6

M3 - Article

VL - 126

SP - 49

EP - 53

JO - Chemistry and Physics of Lipids

T2 - Chemistry and Physics of Lipids

JF - Chemistry and Physics of Lipids

SN - 0009-3084

IS - 1

ER -