Enantioselective Total Synthesis of (+)-Flavisiamine F via Late-Stage Visible-Light-Induced Photochemical Cyclization
By:Tong, Xiaogang; Shi, Bingfei; Liang, Kangjiang; Liu, Qian; Xia, Chengfeng
Angewandte Chemie (International ed. in English)
Published:2019-Apr-08(Epub 2019 Mar 18)
Document Type:Journal Article
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 constructing 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.
Keyword List:alkaloids; asymmetric catalysis; photochemical cyclization; rearrangement; total synthesis
Addresses:Key Laboratory of Medicinal Chemistry for Natural Resource (Ministry of Education and Yunnan Province), State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, China.
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, CAS, Kunming, 650201, Yunnan, China.
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