Enantioselective Total Synthesis of (+)-Flavisiamine F via Late-Stage Visible-Light-Induced Photochemical Cyclization
Tong, Xiaogang1,2; Shi, Bingfei1; Liang, Kangjiang1; Liu, Qian1; Xia, Chengfeng1,2
Corresponding AuthorXia, Chengfeng(xiacf@ynu.edu.cn)
2019-04-08
Source PublicationANGEWANDTE CHEMIE-INTERNATIONAL EDITION
ISSN1433-7851
Volume58Issue:16Pages:5443-5446
AbstractThe 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.
Keywordalkaloids asymmetric catalysis photochemical cyclization rearrangement total synthesis
DOI10.1002/anie.201901241
Indexed BySCI
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000463975300049
Citation statistics
Cited Times:7[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/67629
Collection植物化学与西部植物资源持续利用国家重点实验室
Corresponding AuthorXia, Chengfeng
Affiliation1.Yunnan Univ, Sch Chem Sci & Technol, Minist Educ & Yunnan Prov, Key Lab Med Chem Nat Resource,State Key Lab Conse, Kunming 650091, Yunnan, Peoples R China
2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China
Recommended Citation
GB/T 7714
Tong, Xiaogang,Shi, Bingfei,Liang, Kangjiang,et al. Enantioselective Total Synthesis of (+)-Flavisiamine F via Late-Stage Visible-Light-Induced Photochemical Cyclization[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2019,58(16):5443-5446.
APA Tong, Xiaogang,Shi, Bingfei,Liang, Kangjiang,Liu, Qian,&Xia, Chengfeng.(2019).Enantioselective Total Synthesis of (+)-Flavisiamine F via Late-Stage Visible-Light-Induced Photochemical Cyclization.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,58(16),5443-5446.
MLA Tong, Xiaogang,et al."Enantioselective Total Synthesis of (+)-Flavisiamine F via Late-Stage Visible-Light-Induced Photochemical Cyclization".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 58.16(2019):5443-5446.
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