1,2-Dimethoxyethane → (1S,5R,6R,7R)-7-Benzoyloxy-6-[(E)-(4RS) 4-methyl-3-oxonon-1-en-7-inyl]-2-oxabicyclo[3,3,0]octan-3-one

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Reaction Steps

A solution of 7.56 g of dimethyl-2-oxo-3 -methyl-6-octynylphosphate in 60 ml of dimethoxyethane is to a suspension of 1.33 g of sodium hydride (55% strength in oil) in 65 ml of dimethoxyethane at room temperature. Then the solution is agitated for 30 minutes at room temperature and cooled to -30° C. Subsequently, at -20° C., a solution of 7.66 g of (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one in 84 ml of dimethoxyethane is added thereto and the mixture is stirred for another 2 hours at room temperature. The crude product is isolated analogously to Example (1a), thus obtaining 12.95 g of the title compound as an oil.

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