Antitumor phospholipids: A one-pot introduction of a phosphocholine moiety into lipid hydroxy acceptors

Abstract A high-yielding, 3-step, one-pot conversion of lipid hydroxy acceptors 2 into clinically useful alkylphosphocholines 1 is reported. Reaction of 2 with ethylene chlorophosphite gave phosphite 3 , which underwent oxidation and ring opening with bromine in CH 2 Cl 2 to give (2-bromoethyl)phosphate ester 4 ; hydrolysis of the PBr bond and quaternization of 4 with aqueous trimethylamine generated 1 .