PROSTAGLANDIN ENDOPEROXIDES .25. LEVUGLANDIN-E2 - ENANTIOCONTROLLED TOTAL SYNTHESIS OF A BIOLOGICALLY-ACTIVE REARRANGEMENT PRODUCT FROM THE PROSTAGLANDIN ENDOPEROXIDE PGH2

Diastereoselective 1,4-addition of a vinyl cuprate to a γ-chiral α,β-unsaturated ketone intermediate provides an efficient asymmetric total synthesis of levuglandin E2. While resolution of a racemic precursor provided the second chiral center, preferential generation of the required configuration at the third center of this acyclic synthetic target involved a remarkably stereoselective epimerization. © 1990, American Chemical Society. All rights reserved.