Total synthesis of E1 and E2 isoprostanes by diastereoselective protonation

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. BiBr3 or HF/Py followed by enzymatic hydrolysis of the methyl ester afforded the free E-type isoprostanes.