Potassium Carbonate → Octahydropentalenol

Participants

Reaction Conditions

Reaction Steps

A solution of (E)-6-acetoxy-2-[(mixture of 3α and 3β)-tert-butyldimethylsilyloxyoct-1-enyl]bicyclo[3,3,0]octane (530 mg; prepared as described in Reference Example 24 and predominantly in the 2β-configuration) in methanol (10 ml) was treated with anhydrous potassium carbonate (193 mg). The mixture was heated at 40° C., with stirring, for 24 hours. The methanol was then removed in vacuo and the residue was extracted with dichloromethane (3×10 ml). Concentration of the extract in vacuo gave (E)-2-[(mixture of 3α and 3β)-tert-butyldimethylsilyloxyoct-1-enyl]-6-hydroxybicyclo[3,3,0]octane (430 mg), predominantly in the 2β-configuration.

Provenance & Evidence