A modified Robinson annulation process to α,α-disubstituted-β,γ-unsaturated cyclohexanone system. Application to the total synthesis of nanaimoal

4-Cyano-2-cyclohexenones were found to be susceptible to reductive alkylation reactions, giving the corresponding 2,2-disubstituted-3-cyclohexenone derivatives in a completely regioselective manner. This newly developed methodology has been successfully applied towards the total synthesis, in racemic form, of the marine natural product nanaimoal.