Total Synthesis of Galanthamine and Lycoramine Featuring an Early-Stage C–C and a Late-Stage Dehydrogenation via C–H Activation
Yuna Zhang, Shuna Shen, Hua Fang, Tao Xu
Abstract
Herein, we report a novel strategy toward galanthamine and lycoramine. The concise synthesis was enabled by a Rh-catalyzed gram-scale C-C activation for the tetracyclic carbon framework and a regioselective Pd-catalyzed C-H activation for double-bond introduction. An aqueous-phase Beckmann rearrangement was performed for nitrogen atom insertion. Galanthamine and lycoramine were completed in 11 and 10 steps, respectively.
Topics & Concepts
ChemistryDehydrogenationRegioselectivityNitrogen atomCatalysisStereochemistryCombinatorial chemistryMedicinal chemistryOrganic chemistryRing (chemistry)Chemical synthesis and alkaloidsAlkaloids: synthesis and pharmacologyCatalytic C–H Functionalization Methods