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

Participants

Reaction Steps

A stirred solution of crude (E)-2-[(mixture of 3α and 3β)-tert-butyldimethylsilyloxy-3-cyclohexylprop-1-enyl]-6-hydroxybicyclo[3,3,0]octane (0.36 g; prepared as described in Reference Example 32 and predominantly in the 2β-configuration) in dichloromethane (15 ml) was treated with pyridinium chlorochromate (0.42 g) at 20° C. under an argon atmosphere and stirred for a further period of 3.5 hours. The mixture was then treated with silica gel (2 g) and carefully concentrated in vacuo. The resulting powder was placed onto a column of silica gel and eluted with a mixture of ethyl acetate and hexane (1:4 v/v), to give (E)-2-[(mixture of 3α and 3β)-tert-butyldimethylsilyloxy-3-cyclohexylprop-1-enyl]bicyclo[3,3,0]octan-6-one (0.22 g), predominantly in the 2β-configuration.

Provenance & Evidence