An Enantioselective Synthesis of Platelet-Activating Factors, Their Enantiomers, and Their Analogues from Dand 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-configuration) 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. © 1985, The Pharmaceutical Society of Japan. All rights reserved.