Regioselective and stereospecific cleavage of a terminal oxirane system: A novel synthetic approach to lipid mediator congeners—1,2(2,3)-diacyl-3(1)-halo-sn-glycerols

Glycidyl esters upon treatment with a mixture of carboxylic acid anhydride (CAA) and trimethylsilyl halide (TMSX) in the presence of tetra-n-butylammonium halide (Bu4NX, X = Cl, Br or I) undergo stereospecific and regioselective opening of the oxirane ring to afford mixed-(or mono)-acid 1,2(2,3)-diacyl-3(1)-halo-sn-glycerols in high yields.