3 years ago

Divergent Total Syntheses of (-)-Daphnilongeranin B and (-)-Daphenylline

Hongbin Zhai, Bin Cheng, Yun Li, Huifei Wang, Xinkan Yang, Xiaoming Chen, Houqiang Lv, Jingjing Guo, Cheng Tao, Xiaoru Shao, Jing Zhang, Hai-Jun Zhang
Described herein is the first asymmetric total synthesis of (-)-daphnilongeranin B and bioinspired synthesis of (-)-daphenylline, which has an unusual E-ring embedded in a cage-like framework. The key features include an intermolecular [3+2] cyclization, a late-stage aldol cyclization to install the F ring of daphnilongeranin B, and a bioinspired cationic rearrangement leading to the tetrasubstituted benzene ring of daphyenlline.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201709762

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