Facile synthesis of (Z)-tetracos-5-enoic acid and racemic cis-4-(2-octadecylcyclopropane-1-yl)-butanoic acid.
(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.
Coxon
Geoffrey D
GD
Department of Chemistry, University of Newcastle, Newcastle upon Tyne NE1 7RU, UK.
Douglas
James D
JD
Minnikin
David E
DE
D001419:Bacteria / Q000737:chemistry / Q000648:ultrastructure; D002087:Butyrates / Q000138:chemical synthesis*; D020148:Butyric Acid / Q000138:chemical synthesis*; D002473:Cell Wall / Q000737:chemistry; D005229:Fatty Acids, Monounsaturated / Q000138:chemical synthesis*; D013237:Stereoisomerism
C488657:4-(2-octadecylcyclopropane-1-yl)butanoic acid; D002087:Butyrates; D005229:Fatty Acids, Monounsaturated; D020148:Butyric Acid; C064583:tetracosenoic acid