Synthesis of thiaprostaglandin E1 derivatives.

Abstract

A series of new thiaprostaglandins, 4-thia-, 5-thia-, 6-thia-and 7-thiaprostaglandin E1 methyl esters (3b, 4b, 5b, and 6b), was synthesized by a three-component coupling process using a chiral common synthon, (R)-4-tert-butyldimethylsilyloxy-2-cyclopentenone (1). Among these thiaprostaglandins, 7-thiaprostaglandin E1 methyl ester showed the most potent platelet aggregationinhibiting activity.