1. A Concise Total Synthesis of (−)‐Berkelic Acid.
- Author
-
Cheng, Hong‐Gang, Yang, Zhenjie, Chen, Ruiming, Cao, Liming, Tong, Wen‐Yan, Wei, Qiang, Wang, Qingqing, Wu, Chenggui, Qu, Shuanglin, and Zhou, Qianghui
- Subjects
CHROMANS ,CHIRAL centers ,ACIDS ,NATURAL products - Abstract
Reported here is a concise total synthesis of (−)‐berkelic acid in eight linear steps. This synthesis features a Catellani reaction/oxa‐Michael cascade for the construction of the isochroman scaffold, a one‐pot deprotection/spiroacetalization operation for the formation of the tetracyclic core structure, and a late‐stage Ni‐catalyzed reductive coupling for the introduction of the lateral chain. Notably, four stereocenters are established from a single existing chiral center with excellent stereocontrol during the deprotection/spiroacetalization process. Stereocontrol of the intriguing deprotection/spiroacetalization process is supported by DFT calculations. [ABSTRACT FROM AUTHOR]
- Published
- 2021
- Full Text
- View/download PDF