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 ; PAFs), their enantiomers, and their analogues were efficiently synthesized in a stereochemically unambiguous manner starting from D-and L-tartaric acids as chiral synthons. The enantiomer of C₁₆-PAF (S-comfiguration) showed far less activity than the natural PAF (R-configuration), and the N-methylpiperidine and N-methylpyrrolidine analogues were found to possess much higher activity than natural C₁₆-PAF.