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

Participants

Reaction Conditions

Reaction Steps

The (1S,2RS,5S,6S,7R)-2-hydroxy-3-methylene-6-[(E,3S)-3-t-butyldimethylsilyloxy-l-octenyl]-7-t-butyldimethylsilyloxybicyclo[3.3.0]octane (127 mg, 0.25 mmole) obtained in Example 3 was dissolved in 1 ml of methylene chloride. The solution was cooled to -25° C., and triethylamine (38 mg, 0.375 mmole) and then a solution of methanesulfonyl chloride (43 mg, 0.375 mmole) in 1 ml of methylene chloride were added. The mixture was stirred for 2 hours. Ice water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The separated organic layer was washed with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated. The crude product was subjected to column chromatography (silica gel 15 g; hexane/ethyl acetate=30/1) to give (1S,2RS,5S,6S,7R)-2-methanesulfonyloxy-3-methylene-6-[(E,3S)-3-t-butyldimethylsilyloxy-1-octenyl]-7-t-butyldimethylsilyloxybicyclo[3.3.0]octane (123 mg, 0.21 mmole, 84%).

Provenance & Evidence