Potassium Carbonate → Octahydropentalenol

Participants

Reaction Steps

A mixture of (E)-6-acetoxy-2-[(mixture of 3α and 3β)-tert-butyldimethylsilyloxy-3-cyclohexylprop-1-enyl]bicyclo[3,3,0]octane (0.4 g; prepared as described in Example 31 and predominantly in the 2β-configuration), potassium carbonate (0.15 g) and methanol (10 ml) was heated at 50° C. for 8 hours. The mixture was then cooled and concentrated in vacuo. The resulting residue was extracted with dichloromethane (3×5 ml). Concentration in vacuo of the combined extracts gave (E)-2-[(mixture of 3α and 3β)-tert-butyldimethylsilyloxy-3-cyclohexylprop-1-enyl]-6-hydroxybicyclo[3,3,0]octane, predominantly in the 2β-configuration, in the form of an oil (0.36 g), sufficiently pure enough in the next stage.

Provenance & Evidence