Total Synthesis of (±)-Murrayazoline

The total synthesis of (±)-murrayazoline (1) is described. The characteristic hexa-heterocyclic structure of 1 was constructed by a combination of the intramolecular Friedel−Crafts-type Michael addition and Pd-catalyzed C−O coupling reactions. The N-substituted carbazole component was synthesized in one pot by the double N-arylation of a sterically hindered amine with a dibromobiphenyl derivative.