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

Autor:	James D. Douglas, David E. Minnikin, Geoffrey D. Coxon
Rok vydání:	2003
Předmět:	Bacteria Cyclopropanation Stereochemistry Organic Chemistry Periodic acid Epoxide Stereoisomerism Cell Biology Cleavage (embryo) Biochemistry Fatty Acids Monounsaturated Butyrates chemistry.chemical_compound chemistry Cell Wall Bromide Wittig reaction Butyric Acid Molecular Biology
Zdroj:	Chemistry and Physics of Lipids. 126:49-53
ISSN:	0009-3084
DOI:	10.1016/s0009-3084(03)00092-6
Popis:	(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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::bac9445e7fc973fda2328c714ac54995 https://doi.org/10.1016/s0009-3084(03)00092-6 Zobrazit plný text záznamu Full Text from ScienceDirect