HCID 131717629, compound → HCID 86745710, compound

Participants

Reaction Conditions

Reaction Steps

(1S,5S,6S,7R)-3-[4-Methoxycarbonyl-1(EZ)-butenyl]-6-[4(RS)-fluoro-3-oxo-(E )-1-octenyl]-7-tetrahydropyranyloxybicyclo[3.3.0]oct-2-ene (5) (0.109 g) was dissolved in acetone in an autoclave. Into the solution, a tricarbonyl chromium/methyl benzoate complex (0.023 g) was added. The mixture was degassed and the content was stirred under a hydrogen atmosphere (70 kg/cm2) at 125° C. for 20 hours. The reaction mixture was concentrated under reduced pressure. A crude product obtained was chromatographed (hexane/ethyl acetate=10/1-7/1 to give (1S,2R,3R,5S)-7(E)-(4-carbomethoxybutylidene)-2-[4(RS )-fluoro-3-oxo-octyl]-3-tetrahydropyranyloxy-bicyclo[3.3.0]octane (11) as a colorless oily product. Yield: 0.157 g (99%)

Provenance & Evidence