153953-91-4Relevant academic research and scientific papers
Syntheis of methyl (E,Z,Z)-2(or 4 or 6),9,12-octadecatrienoate and methyl (E,Z,Z)-2(or 6 or 8),11,14-eicosatrienoate
Klok, R.,Moehlmann, W. M. M.,Wolf, L. van der,Pabon, H. J. J.
, p. 132 - 137 (2007/10/02)
For studies into the relationship between their physical properties and chemical structure, several polyunsaturated fatty acids related to (Z,Z,Z)-6,9,12-octadecatrienoic acid and (Z,Z,Z)-8,11,14-eicosatrienoic acid were synthesized.Methyl (E,Z,Z)-2,11,14-eicosatrienoate and methyl (E,Z,Z)-2,9,12-octadecatrienoate were prepared by E-stereoselective coupling of (methoxycarbonylmethylene)triphenylphosphorane with (Z,Z)-9,12-octadecadienal and (Z,Z)-7,10-hexadecadienal respectively.The synthesis of methyl (E,Z,Z)-4,9,12-octadecatrienoate started from 2,7-octadiyn-1-ol which was reduced with lithium aluminium hydride.The (E)-2-octen-7-yn-1-ol thus obtained coupled with 1-bromo-2-octyne to give (E)-2-hexadecene-7,10-dyin-1-ol.This was converted into 1-chloro-(E)-2-hexadecene-7,10-diyne, which via malonic ester synthesis yielded (E)-4-octadecene-9,12-diynoic acid.Stereospecific hydrogenation and esterification finally afforded the desired compound, from which methyl (E,Z,Z)-6,11,14-eicosatrienoate was obtained by chain elongation.Methyl (E,Z,Z)-6,9,12-octadecatrienoate was synthesized from 1,4-dichloro-(E)-2-butene which was converted into (E)-4-octen-7-ynoic acid.Coupling the latter with 1-bromo-2-octyne, esterification and reduction yielded (E)-4-hexadecene-7,10-diyn-1-ol.Conversion into the corresponding chloro compound and stereospecific hydrogenation yielded 1-chloro-(E,Z,Z)-4,7,10-hexadcatriene.Malonic ester sythesis finally afforded the desired compound.The synthesis of methyl (E,Z,Z)-8,11,14-eicosatrienoate started from 2-octyne-1,8-diol which was reduced with lithium aluminium hydride; the resulting (E)-octene-1,8-diol was converted into 1,8-dichloro-(E)-2-octene.The latter was coupled with 1,4-decadiyne to give 1-chloro-(E)-6-octadecene-9,12-diyne, which was hydrogenated stereospecifically.Malonic ester synthesis finally completed the synthesis.
