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An enantioselective synthesis of 12-epi-PGF2 α (3) and 12,15-diepi-PGF2 α (4), PG-like compounds that are probably generated in vivo by nonenzymatic, free-radical-induced peroxidation of arachidonic acid, has been achieved starting from the commercially available Corey lactone (9). The key strategy involves SmI2 reduction of the γ,δ-epoxy-α,β-unsaturated ester 7, followed by in situ trapping with hexanal; subsequent hydrogenation and decarboxylation affords the stereoselective construction of the lower side chain. This new method is expected to provide a convenient access to various PG-like isoprostanes derived from oxidation of arachidonic acid and cis-4,7,10,13,16,19-docosahexaenoic acid.

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Enantioselective Synthesis of 12-epi-PGF 2α and 12,15-diepi-PGF 2α .