Total Synthesis of (–)-Strempeliopine via Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation

Reported herein a concise and enantioselective total synthesis of Schizozygine alkaloids (–)-strempeliopine. This synthetic strategy features a palladium-catalyzed decarboxylative asymmetric allylic alkylation of N-benzoyl lactam to set up the absolute configuration at the C20 position, a highly diastereoselective one-pot Bischler-Napieralski/lactamization and iminium reduction sequence for the construction of the pentacyclic core structure, and a late-stage dearomative addition of indole leading to the challenging hexacyclic indoline framework with complete control of correct four neighbouring stereocenters.