Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 16, Pages 5443-5446Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201901241
Keywords
alkaloids; asymmetric catalysis; photochemical cyclization; rearrangement; total synthesis
Categories
Funding
- National Natural Science Foundation of China [21572236, 21602194, 21871228]
- Natural Science Foundation of Yunnan Province [2018FY001015]
- West Light Foundation of the Chinese Academy of Sciences
- Program for Changjiang Scholars and Innovative Research Team in University [IRT_17R94]
- Advance Analysis and Measurement Center of Yunnan University
Ask authors/readers for more resources
The structural features Kopsia alkaloids; in particular multiple all-carbon quaternary stereocenters in a caged and strained polycyclic skeleton, poses particular challenges for enantioselective total synthesis. Herein, we reported the first total synthesis of (+)-flavisiamine F The synthetic approach involved a room-temperature Overman rearrangement for introducing the chiral amine at C21, a TMS-promoted ketal Claisen rearrangement for constnicting the all-carbon quaternary stereocenter at C20, and a late-stage visible-light-induced photochemical cyclization for establishing the all-carbon quaternary stereocenter at C7.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available