Ring-Closing Alkyne Metathesis: Application to the Stereoselective Total Synthesis of Prostaglandin E2-1,15-Lactone

Abstract

The first total synthesis of a biologically relevant natural product (prostaglandin E2-1,5-lactone; see picture) by ring-closing diyne metathesis followed by Lindlar reduction is reported. This conceptually novel strategy allows the stereoselective formation of macrocyclic Z alkenes which cannot be accessed stereoselectively by conventional ring-closing olefin metathesis.