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 |
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| Authors: | Stamatov Stephan D Stawinski Jacek |
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| Institution: | Department of Chemical Technology, University of Plovdiv, 24 Tsar Assen St., Plovdiv 4000, Bulgaria. js@organ.su.se |
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| Abstract: | Glycidyl esters upon treatment with a mixture of carboxylic acid anhydride (CAA) and trimethylsilyl halide (TMSX) in the presence of tetra-n-butylammonium halide (Bu(4)NX, 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. |
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