Total Synthesis of (±)-Aspidophylline A

A total synthesis of aspidophyllineA, a pentacyclic akuammiline-type monoterpene indole alkaloid, is described. The synthesis features: 1)rapid access to a fully functionalized dihydrocarbazole through the desymmetrization of readily available 2-allyl-2-(o-nitrophenyl)cyclohexane-1,3-dione; 2)an intramolecular azidoalkoxylation of an enecarbamate to install both the furoindoline ring and the azido functionality; and 3)an intramolecular Michael addition for the construction of the 2-azabicyclo[3.3.1]nonane ring system.