249890-38-8Relevant articles and documents
Enantioselective synthesis of 12-epi-PGF(2α) and 12,15-diepi-PGF(2α)
Lai, Sheng,Lee, Dongreyoul,U, Jong Sun,Cha, Jin Kun
, p. 7213 - 7217 (1999)
An enantioselective synthesis of 12-epi-PGF(2α) (3) and 12,15-diepi- PGF(2α) (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.