Potassium Carbonate → 3,3a,4,5,6,6a-hexahydro-2H-pentalen-1-one

Participants

Reaction Conditions

Reaction Steps

A stirred solution of (E)-2-[(mixture of 3α and 3β)-tert-butyldimethylsilyloxyoct-1-enyl]-6-hydroxybicyclo[3,3,0]octane (430 mg prepared as described in Reference Example 25 and predominantly in the 2β-configuration) in dry dichloromethane (15 ml) was treated with potassium acetate (127 mg), potassium carbonate (110 mg) and pyridinium chlorochromate (561 mg), and the mixture was stirred for 150 minutes at 20° C. A further quantity of pyridinium chlorochromate (120 mg) was then added and the mixture was stirred for a further period of 1 hour. The mixture was then concentrated in vacuo and subjected to chromatography on a silica gel column, using a mixture of ethyl acetate and hexane (1:4 v/v) as eluant, to give (E)-2-[(mixture of 3α and 3β)-tertbutyldimethylsilyloxyoct-1-enyl]bicyclo[3,3,0]octan-6-one (330 mg), predominantly in the 2β-configuration.

Provenance & Evidence