Formal Synthesis of (-)- and (+)-Phalarine

Significance

Phalarine is a synthetically challenging indole-related alkaloid with interesting ­interlocking ring systems. Presented herein is a formal synthesis of both (-)- and (+)-phalarine pre-cursors via a diastereoselective oxidative cyclization of intermediate H, mediated by hypervalent iodine. Intermediate H in turn is formed from a ­series of palladium cross-coupling reactions.