Total Syntheses of Bisdehydroneostemoninine and Bisdehydrostemoninine by Catalytic Carbonylative Spirolactonization
Dr. Kaiqing Ma
Department of Chemistry, Center for Cancer Research, and Institute for Drug Discovery, Purdue University, West Lafayette, Indiana, 47907 USA
Modern Research Center for Traditional Chinese Medicine, of Shanxi University, Taiyuan, 03006 Shanxi, China
These authors contributed equally to this work.
Search for more papers by this authorXianglin Yin
Department of Chemistry, Center for Cancer Research, and Institute for Drug Discovery, Purdue University, West Lafayette, Indiana, 47907 USA
These authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Prof. Mingji Dai
Department of Chemistry, Center for Cancer Research, and Institute for Drug Discovery, Purdue University, West Lafayette, Indiana, 47907 USA
Search for more papers by this authorDr. Kaiqing Ma
Department of Chemistry, Center for Cancer Research, and Institute for Drug Discovery, Purdue University, West Lafayette, Indiana, 47907 USA
Modern Research Center for Traditional Chinese Medicine, of Shanxi University, Taiyuan, 03006 Shanxi, China
These authors contributed equally to this work.
Search for more papers by this authorXianglin Yin
Department of Chemistry, Center for Cancer Research, and Institute for Drug Discovery, Purdue University, West Lafayette, Indiana, 47907 USA
These authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Prof. Mingji Dai
Department of Chemistry, Center for Cancer Research, and Institute for Drug Discovery, Purdue University, West Lafayette, Indiana, 47907 USA
Search for more papers by this authorGraphical Abstract
Core strength: The first total syntheses of the stemona alkaloids bisdehydroneostemoninine and bisdehydrostemoninine are reported. The synthesis features a novel palladium-catalyzed carbonylative spirolactonization to rapidly construct the oxaspirolactone moiety and a Lewis acid promoted tandem Friedel–Crafts cyclization and lactonization to form the 5-7-5 tricyclic core of the target alkaloids.
Abstract
The first total syntheses of the stemona alkaloids bisdehydroneostemoninine and bisdehydrostemoninine in racemic forms have been achieved. The synthetic strategy features a novel palladium-catalyzed carbonylative spirolactonization of a hydroxycyclopropanol to rapidly construct the oxaspirolactone moiety. It also features a Lewis acid promoted tandem Friedel–Crafts cyclization and lactonization to form the 5-7-5 tricyclic core of the target stemona alkaloids.
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