Oxidative Cyclization of Kynuramine and Ynones Enabling Collective Syntheses of Pyridoacridine Alkaloids

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A cerium(III)-catalyzed oxidative cyclization of kynuramine and ynones has been reported as a key reaction in the total synthesis of marine pentacyclic pyridoacridine alkaloids featuring different ring connectivity patterns. The formation of tricyclic benzonaphthyridine rings was identified in the oxidative process. By combining with an intramolecular acylation and the chemoselective late-stage functionalization of pyridine rings, different approaches with 4–10 steps have been designed to accomplish the synthesis of alkaloids demethyldeoxyamphimedine ( 1 ), amphimedine ( 2 ), meridine ( 3 ), isocystodamine ( 4 ), N -methylisocystodamine ( 5 ), N -hydroxymethylisocystodamine ( 6 ), 9-hydroxyisoacididemin ( 7 ), neolabuanine A ( 8 ), and ecionine A ( 9 ).