AN EFFICIENT SYNTHESIS OF THE ANTISECRETORY PROSTAGLANDIN ENISOPROST

An efficient 11-step synthesis of the antisecretory prostaglandin enisoprost starting with (Z,Z)-1,5-cyclooctadiene has been developed. The key steps in the synthesis are a selective ozonolysis of (Z,Z)-1,5-cyclooctadiene, a zinc chloride catalyzed rearrangement of a furanylcarbinol, and a coupling reaction of a suitably substituted cyclopentenone with a dilithiocyanocuprate reagent derived from 4-methyl-1-octyn-4-ol