Enantiocomplementary total asymmetric syntheses of prostaglandin A2

Abstract

Both enantiomers of the racemic ketone (4) have been converted into (+)-PGA₂ by utilizing two different synthetic pathways. In one route the reaction of the strained tricyclic ketone (8) with the cuprate reagent (9) was the critical step, while in the ‘enantiocomplementary’ process the S_N′ reaction of the same cuprate reagent with the epoxide (16) was the crucial transformation.