HCID 131717629, compound → HCID 18648699, compound

Participants

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) (0.094 g) was dissolved in ethyl acetate. Into the solution, palladium(5 wt %)/carbon (0.0094 g) was added and the mixture was stirred under reaction mixture was filtered, and the filtrate was evaporated under reduced pressure. Obtained crude product was chromatographed using a silica gel treated with silver nitrate (15 wt %) (hexane/ethyl acetate=12/1-9/1) to give (1S,5S,6R,7R)-3-(4-methoxycarbonyl)-6-[4(RS)-fluoro-3-oxooctyl]- 7-tetrahydropyranyloxybicyclo[3.3.0]oct-2-ene (6) as a pale yellow oily product. Yield: 0.042 g (44%)

Provenance & Evidence