Acetic Anhydride → (1S,2RS,5S,6S,7R)-2-acetoxy-3-methylene-6-[(E,3S)-3-t-butyldimethylsilyloxy-l-octenyl]-7-t-butyldimethylsilyloxybicyclo[3.3.0]octane

Participants

Reaction Steps

Acetic anhydride (0.5 ml) and pyridine (0.5 ml) were added to 95 mg (0.187 mmole) of (1S,2RS,5S,6S,7R)-2-hydroxy-3-methylene-6-[(E,3S)-3-t-butyldimethylsilyloxy-1-octenyl]-7-t-butyldimethylsilyloxybicyclo[3.3.0]octane obtained in Example 3, and the mixture was stirred at room temperature for 10 hours. The reaction mixture was concentrated under reduced pressure, and then subjected to column chromatography (silica gel 20 g, hexane/ethyl acetate=19/1) to give (1S,2RS,5S,6S,7R)-2-acetoxy-3-methylene-6-[(E,3S)-3-t-butyldimethylsilyloxy-l-octenyl]-7-t-butyldimethylsilyloxybicyclo[3.3.0]octane (101 mg, 0.184 mmole, 98%).

Provenance & Evidence