Total Synthesis of Acoapetaludine A Enabled by a Rhodium-Catalyzed Domino Cyclization

A rhodium-catalyzed asymmetric domino cyclization was developed, which enables the efficient assembly of highly strained bridged tricyclic scaffolds. Taken together with a deprotection/retro-aldol/intramolecular Mannich reaction cascade and a diastereocontrolled intramolecular Diels–Alder cycloaddition, the first total synthesis of C20-diterpenoid alkaloid acoapetaludine A has been achieved in a concise and practical manner.