Document Detail

A divergent synthesis of [1-14C]-mono-E isomers of fatty acids.
MedLine Citation:
PMID:  14625078     Owner:  NLM     Status:  MEDLINE    
A convenient synthesis of [1-14C]-mono-trans fatty acid using olefin inversion as a key-step is described. This methodology allows for a facile synthesis of [1-14C]-labelled mono-trans analogues of oleic, linoleic and linolenic acids. As an example, only eleven steps were necessary to obtain the [1-14C]-mono-E isomers of linolenic acid from its commercial all-Z form. In the first step, Barton's decarboxylation procedure yielded a bromo intermediate. Epoxidation of this compound resulted in the formation of three monoepoxides, which could be separated by HPLC. After identification by 1H NMR and MS, the pure monoepoxides were then subjected to inversion consisting of a stereospecific deoxygenation followed by a beta-elimination step. Finally, the labelling was introduced by substitution of the bromine by a [14C]-cyano group followed by hydrolysis.
D Georgin; F Taran; C Mioskowski
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Chemistry and physics of lipids     Volume:  125     ISSN:  0009-3084     ISO Abbreviation:  Chem. Phys. Lipids     Publication Date:  2003 Sep 
Date Detail:
Created Date:  2003-11-19     Completed Date:  2004-05-12     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0067206     Medline TA:  Chem Phys Lipids     Country:  Ireland    
Other Details:
Languages:  eng     Pagination:  83-91     Citation Subset:  IM    
CEA/Saclay, DSV-DBJC-SMMCB-bât 547-Saclay-F-91191 Gif sur Yvette Cedex, France.
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MeSH Terms
Chromatography, High Pressure Liquid
Epoxy Compounds / chemistry
Fatty Acids / chemical synthesis*,  chemistry*
Molecular Structure
Reg. No./Substance:
0/Epoxy Compounds; 0/Fatty Acids

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