HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS		QUICK SEARCH:   [advanced] Author: Keyword(s): Year:  Vol:  Page:

This Article Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Services Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Download to citation manager Citing Articles Citing Articles via HighWire Citing Articles via Google Scholar Google Scholar Articles by Stoffel, W. Articles by Pruss, H. D. Search for Related Content PubMed PubMed Citation Articles by Stoffel, W. Articles by Pruss, H. D. Social Bookmarking                      What's this?

Journal of Lipid Research, Vol. 8, 196-201, May 1967
Copyright © 1967 by Lipid Research, Inc.

Synthesis of eicosa-2-trans-8, 11, 14-all cis-tetraenoic acid-3-¹⁴C and dl-3-hydroxy eicosa-8, 11, 14-all cis-trienoic acid-3-¹⁴C

W. Stoffel and H. D. Pruss

Physiologisch-Chemisches Institut der Universität Köln, Köln, West Germany

A general procedure for the synthesis of 2-trans polyenoic fatty acids and of dl-3-hydroxypolyenoic acids is described. The 2-trans acids are prepared by LiAlH₄ reduction of a suitable polyenoic fatty acid ester to the alcohol, formation of the tosylate, oxidation to the aldehyde, and Doebner condensation of the latter with malonic acid. The 3-hydroxy acids are obtained by reaction of the acyl chloride of a suitable polyenoic acid with the sodium enolate of methyl acetoacetate and sodium methoxide to give the 3-keto ester, the keto group of which is reduced with sodium borohydride to the alcohol. These procedures were applied to the synthesis of eicosa-2-trans-8, 11, 14-all cis-tetraenoic acid-3-¹⁴C and dl-3-hydroxy eicosa-8, 11, 14-trienoic acid-3-¹⁴C.

Supplementary key words ¹⁴C-labeled polyenoic acids • eicosa-2-trans-8,11,14-all cis-tetraenoic acid • dl-3-hydroxy eicosa-8,11,14-trienoic acid

Submitted on November 9, 1966
Accepted on January 19, 1967

CiteULike    Complore    Connotea    Del.icio.us    Digg    Reddit    Technorati    What's this?

This article has been cited by other articles:

				D. L. Luthria, S. P. Baykousheva, and H. Sprecher Double Bond Removal from Odd-numbered Carbons during Peroxisomal [IMAGE]-Oxidation of Arachidonic Acid Requires both 2,4-Dienoyl-CoA Reductase and [IMAGE][IMAGE],[IMAGE][IMAGE]-Dienoyl-CoA Isomerase J. Biol. Chem., June 9, 1995; 270(23): 13771 - 13776. [Abstract] [Full Text] [PDF]