Enantio-complementary total asymmetric syntheses of prostaglandin E2 and prostaglandin F2?

Abstract

The racemic ketone (6) was converted into the diastereoisomeric alcohols (7) and (8) using actively fermenting yeast. These alcohols were separated and converted into the bromohydrins (–)-(9) and (+)-(9). The bromohydrin (–)-(9) was converted into prostaglandin E₂(1) and prostaglandin F_2α(2) by reaction of the chiral cuprate reagent (15) with the tricyclic ketone (10), while the bromohydrin (+)-(9) was converted into the prostaglandins by reaction of the epoxyacetal (11) with the same cuprate reagent (15).