HCID 131717632, compound → HCID 86745716, compound

Participants

Reaction Conditions

Reaction Steps

(1S,5S,6S,7R)-3-[4-Methoxycarbonyl-1(EZ)-butenyl]-6-[4,4-difluoro-3(RS) hydroxy-(E)-1-octenyl]-7-tetrahydropyranyloxybicyclo[3.3.0]oct-2ene (17) (0.184 g) was dissolved in acetone and the solution was placed in an autoclave, into which tricarbonyl chromium/methyl benzoate complex (0.021 g) was added, and then the autoclave was degassed. The mixture in the autoclave was stirred under hydrogen pressure (70 kg/cm2) at 120° C. for 15 hours. The reaction mixture was concentrated under reduced pressure, and the obtained crude product was purified on column chromatography (hexane/ethyl acetate=7/2-3/1) to give (1S,2S,3R,5S)-(E)-7-(4-methoxycarbonylbutylidene)-2-[4,4-difluoro-3(RS)-hydroxy-(E) -1-octenyl]-3-tetrahydropyranyloxybicyclo[3.3.0]octane (18) as a colorless oily product. Yield: 0.175 g (95%)

Provenance & Evidence