Novel synthesis of prostaglandin-E2 involving regioselective ring opening of a 2,3-endo-epoxybicyclo[3.2.0]heptan-6-one acetal with a mixed organocuprate reagent
Abstract
The epoxyacetal (2) is ring opened by appropriate organometallic reagents regioselectively to afford the acetals (15) and (17) in high yield; the acetal (15) was transformed into the prostaglandin-F2α precursor (4) in two steps, while (17) furnished the prostaglandin-E2 intermediate (24) in three steps.