title: Direct synthesis of plasmenylcholine from allyl-substituted glycerols.
abstract: We report a new method for the facile preparation of plasmenylcholine via reaction of lithioalkoxy allyl intermediates with 1-iodoalkanes as the key step in the stereoselective formation of 1'-(Z)-alkenyl glyceryl ethers. The allyl anion intermediate is prepared by treating mono- or disiloxy-protected 1-allylglycerol precursors with s-BuLi at -65 to -80 degrees C. Subsequent addition of 1-iodoalkane solutions at low temperature gives moderate yields of gamma-coupled, Z-vinyl ethers as the major product and alpha-coupled product as the minor component. Several different preparative strategies for the total synthesis of plasmalogens are enabled by this simple transformation.
authors.affiliation: Department of Chemistry, Purdue University, West Lafayette, Indiana 47907-1393, USA.
authors.forename: Junhwa
authors.initials: J
authors.lastname: Shin
authors.forename: David H
authors.initials: DH
authors.lastname: Thompson
mesh_terms: D005990:Glycerol / Q000031:analogs & derivatives* / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010955:Plasmalogens / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007202:Indicators and Reagents; D010955:Plasmalogens; C032459:choline plasmalogens; D005990:Glycerol