Total Syntheses of Galanthamine and Lycoramine via a Palladium-Catalyzed Cascade Cyclization and Late-Stage
Ya-Ping Chang1, Xia Ma1, Hui Shao1
1Key Laboratory of Applied Surface and Colloid Chemistry & School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 West Chang'an Ave, Xi'an, 710119, China.
Abstract:
Herein, we report the highly efficient total syntheses of galanthamine and lycoramine from a common tetracyclic intermediate. This concise synthetic route features a two-phase strategy, which includes the early-stage rapid construction of a tetracyclic skeleton followed by the late-stage selective reorganization of the tetracyclic skeleton. Key to the success of this strategy are a palladium-catalyzed carbonylative cascade annulation, a DDQ-mediated intramolecular regioselective oxidative lactamization, as well as a BF3·Et2O-promoted reorganization of the bridged tetracyclic skeleton.
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