Synthetic Studies toward (±)-Scandine Using Fe-Catalyzed Carbonyl Olefin Metathesis and Double α-Vinylation of Ketone.

The complete carbon skeleton of a pentacyclic alkaloid, (±)-scandine, which lacks the B ring, was synthesized using a new approach. Major features include forming the C ring through Schindler's FeCl3-catalyzed carbonyl-olefin metathesis and adding the characteristic divinyl substituents via Rawal's recently developed protocol for α-vinylation of ketone.