249890-40-2

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 249890-37-7 (1S,5R,7R,2'R,S,3'R,S)-7-hydroxy-6-[(E,Z)-3'-hydroxyoct-2'-carbobenzyloxy-1'-ylidene]-2-oxabicyclo[3.3.0]octan-3-one 
• 249890-38-8 (1S,5S,6S,7R)-6,7-epoxy-6-[(E)-2'-carbobenzyloxy-1'-vinyl]-2-oxabicyclo[3.3.0]octan-3-one 
• 15097-38-8 (carbobenzyloxymethylene)triphenylphosphorane 
• 51260-12-9 (1S,5S)-3-oxo-2-oxabicyclo<3.3.0>oct-6-en-6-carbaldehyde 
• 62158-44-5 (1S,5R)-6-hydroxymethyl-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 249890-39-9 (1S,5S,6R,7R)-6,7-epoxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one 
• 39746-01-5 (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one 

Relevant academic research and scientific papers

Enantioselective synthesis of 12-epi-PGF(2α) and 12,15-diepi-PGF(2α)

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.