Proline-Catalyzed Cyclization Reaction for the Synthesis of Naphthostyrils: Application to the Total Synthesis of Prioline

A new method for the synthesis of naphthostyrils is described. In this method, a sequential Stille coupling and proline‐catalyzed cyclization procedure is employed for the reaction of 4‐bromooxindoles and β‐tributylstannyl‐α,β‐unsaturated ketones. The utility of this methodology is demonstrated in the first total synthesis of prioline from a simple 2‐isopropylphenol.