An efficient 11-step syntheais of the antisecretory prostaglandin enisoprost starting with (Z, Z)-1, 5-cyclooctadene has been developed. The key steps in the synthesis are a selective ozonolysis of (Z, Z)-1, 5-~ yclooctadiene, 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-4-01.
[Kling, Marcel R.; McNaughton-Smith, Grant A.; Taylor, Richard J. K. Journal of the Chemical Society, Chemical Communications, 1993 , # 21 p. 1593 - 1595]
