A Highly Efficient and Convergent Reaction for the Synthesis of Bridgehead Enone-Containing Polycyclic Ring Systems

A triple-domino reaction involving a Grignard addition, an oxy-Cope rearrangement, and a Dieckmann cyclization provides olefin-containing polycyclic bridgehead compounds from simple vinylated β-ketoesters [Eq. (1)]. This general methodology allows the quick preparation of ring systems not easily accessed by other methods.