An enantioselective synthesis of platelet-activating factors, their enantiomers, and their analogues from D- and L-tartaric acids.

Abstract

Acetyl glyceryl ether phosphorylcholines (platelet-activating factors; PAF), their enantiomers and their analogs were efficiently synthesized in a stereochemically unambiguous manner starting from D- and L-tartaric acids as chiral synthons. The enantiomer of C16-PAF (S-configuration) showed far less activity than the natural PAF (R-configuration), and the N-methylpiperidine and N-methylpyrrolidine analogs possessed much higher activity than natural C16-PAF.