Total synthesis of E 1 and E 2 isoprostanes by diastereoselective protonation

Abstract

A short total synthesis of the E-type isoprostanes has been achieved using a two-component coupling process combined with a diastereoselective protonation under reagent control. Mild cleavage of the silyl protective groups with cat. BiBr 3 or HF/Py followed by enzymatic hydrolysis of the methyl ester afforded the free E-type isoprostanes.