Synthesis of the diazatricyclic core of the marine alkaloids madangamines

A new approach to synthesize the madangamine core structure is described. The synthesis involves intramolecular N,O-acetalization of the keto-aminophenol which allows rapid construction of the 2-azabicyclo3.3.1]nonane skeleton with a quaternary carbon center at C4. This strategy also demonstrates the utility of such approach in the stereoselective construction of the central diazatricyclic core found in the madangamine alkaloids.