Abstract
Sequential treatment of bicyclic γ-cyano-α,β-unsaturated ketone 2, readily achieved by Robinson annulation of α-cyano ketone 1 with lithium naphthalenide (LN) and 1,4-diiodobutane or 1,5-diiodopentane gave, in one pot, spiro product 3 in a highly regioselective manner. The dienolate intermediate of the above reductive decyanation process could also be trapped with diethyl chlorophosphonate to give dienyl phosphate 4. Under Lewis acid catalysis conditions, treatment of phosphate 4 with dienophiles gave the highly functionalized Diels-Alder adduct such as compound 5. The details of the investigation into the generality and scope of the above-mentioned transformations constitute the body of this thesis.