Stereocontrolled synthesis of (7E,9Z)-[9,10-2H]-conjugated linoleic acid

Abstract

To study the metabolism of minor conjugated linoleic acid isomers (CLAs), (7E,9Z)-[9,10-2H] CLA was prepared in three steps from a conjugated enyne precursor. In the labelling step, deuterium atoms were introduced by partial reduction of the triple bond using deuterated disiamylborane and acetic acid-d4. Deuterated (7E,9Z) CLA was obtained with high isotopic enrichment (>99%) and purity greater than 95%. Copyright 頲004 John Wiley & Sons, Ltd.