Total Synthesis of Calophyline A
Dr. Guang Li
School of Pharmaceutical Sciences, Tsinghua University, Beijing, 100084 China
These authors contributed equally to this work.
Search for more papers by this authorXiaoni Xie
School of Pharmaceutical Sciences, Tsinghua University, Beijing, 100084 China
These authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Prof. Dr. Liansuo Zu
School of Pharmaceutical Sciences, Tsinghua University, Beijing, 100084 China
Collaborative Innovation Center for Biotherapy, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu, 610041 China
Search for more papers by this authorDr. Guang Li
School of Pharmaceutical Sciences, Tsinghua University, Beijing, 100084 China
These authors contributed equally to this work.
Search for more papers by this authorXiaoni Xie
School of Pharmaceutical Sciences, Tsinghua University, Beijing, 100084 China
These authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Prof. Dr. Liansuo Zu
School of Pharmaceutical Sciences, Tsinghua University, Beijing, 100084 China
Collaborative Innovation Center for Biotherapy, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu, 610041 China
Search for more papers by this authorAbstract
Reported herein is the total synthesis of calophyline A, an indoline natural product possessing distinct ring connectivity which has not been synthesized previously. The synthetic route features several key transformations, including an aza-pinacol rearrangement to construct the nitrogen-containing bridged [3.2.2] bicycle, a Heck cyclization to assemble the fused 6/5/6/5 ring system, and a challenging late-stage aldol reaction to generate both a neopentyl quaternary stereogenic center and an oxygen-containing bridged [3.2.1] bicycle.
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