Facile syntheses for (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-nonadecadienoic acid, and (5Z, 9Z)-5,9-eicosadienoic acid through a common synthetic route
Nm. Carballeira et al., Facile syntheses for (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-nonadecadienoic acid, and (5Z, 9Z)-5,9-eicosadienoic acid through a common synthetic route, CHEM PHYS L, 100(1-2), 1999, pp. 33-40
The Delta 5,9 fatty acids (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-non
adecadienoic acid, and (5Z,9Z)-5,9-eicosadienoic acid were synthesized for
the first time in four steps (9-12% overall yield) starting from commercial
ly available 2-(2-bromoethyl)-1,3-dioxoiane. The synthetic approach provide
d enough material to corroborate the structure and stereochemistry of (5Z,9
Z)-5,9-nonadecadienoic acid which was recently identified in the flowers of
Malvaviscus arboreus (Malvaceae). The novel phospholipids 1-hexadecanoyl-2
-[(5Z,9Z)-5,9-eicosadienoyl]-sn-glycero-3-phosphocholine and 1-octadecanoyl
-2-[(5Z,9Z)-5,9-eicosadienoyl]-sn-glycero-3-phosphocholine were also synthe
sized from commercially available L-alpha-phosphatidylcholine (egg yolk) an
d characterized by positive ion electrospray mass spectrometry. These are t
he first examples of unsymmetrical phospholipids with saturated fatty acids
at the sn-l position and Delta 5,9 fatty acids at the sn-2 position. (C) 1
999 Elsevier Science Ireland Ltd. All rights reserved.