Improved plasmalogen synthesis using organobarium intermediates.
An improved synthesis of plasmalogen type lipids is described. Transmetalation of lithioalkoxy allyl intermediates with BaI(2) and subsequent alkylation with 1-iodoalkanes enables the stereoselective formation of O-(Z)-alkenyl ether as precursors for the synthesis of plasmenyl- and bisplasmenylcholines. This method provides a simple and adaptable approach for the stereocontrolled synthesis of plasmenyl derivatives with variations at the sn-1, sn-2, and sn-3 positions of the glycerol backbone.
Van den Bossche
Jeroen
J
Department of Chemistry, 560 Oval Drive, Purdue University, West Lafayette, Indiana 47907, USA.
Shin
Junhwa
J
Thompson
David H
DH
D017609:Barium Compounds / Q000737:chemistry*; D002794:Choline / Q000737:chemistry; D015394:Molecular Structure; D009930:Organic Chemicals / Q000737:chemistry*; D010955:Plasmalogens / Q000138:chemical synthesis* / Q000737:chemistry
D017609:Barium Compounds; D009930:Organic Chemicals; D010955:Plasmalogens; D002794:Choline