Synthesis of the 4-Azatricyclo[5.2.2.04,8]undecan-10-one Core of Daphniphyllum Alkaloid Calyciphylline A Using a Pd-Catalyzed Enolate Alkenylation

[reaction: see text] The ABC ring system of the natural product calyciphylline A has been synthesized. The key steps were a palladium-catalyzed intramolecular coupling of an amino-tethered vinyl bromide with a ketone using potassium phenoxide as the base to generate the C-ring and a hydroxyl-directed hydrogenation of an exocyclic double bond to give the azatricyclic ketone 1.