SYNTHESIS OF METHYL (5Z,8Z,11E,14Z,17Z)-EICOSAPENTAENOATE AND (5Z,8Z,11E,14Z,17E)-EICOSAPENTAENOATE (EPA DELTA-11T AND DELTA-11T,17T)

Authors
VATELE JM DOAN HD FENET B CHARDIGNY JM SEBEDIO JL
Citation
Jm. Vatele et al., SYNTHESIS OF METHYL (5Z,8Z,11E,14Z,17Z)-EICOSAPENTAENOATE AND (5Z,8Z,11E,14Z,17E)-EICOSAPENTAENOATE (EPA DELTA-11T AND DELTA-11T,17T), Chemistry and physics of lipids, 78(1), 1995, pp. 65-70
Citations number
22
Categorie Soggetti
Biology
Journal title
Chemistry and physics of lipids → ACNP
ISSN journal
00093084
Volume
78
Issue
1
Year of publication
1995
Pages
65 - 70
Database
ISI
SICI code
0009-3084(1995)78:1<65:SOM(A(>2.0.ZU;2-Q
Abstract
The ylide of [(E)-6-(tetrahydropyranyloxy)hex-3-enyl] iodide, a common intermediate in the synthesis of EPA Delta 11t and Delta 11t,17t was condensed with (E)- or (Z)-3-hexenal to afford a C12 trienic ether. Af ter transformation of the tetrahydropyranyl ether function into a phos phonium salt in four steps, a second Wittig reaction between the ylide of this salt and a C8 (Z)-unsaturated aldehyde ester provided the tit le compounds with a purity > 95%.