Enantioselective Total Synthesis of (+)-Flavisiamine F via Late-Stage Visible-Light-Induced Photochemical Cyclization

doi:10.1002/anie.201901241

	Enantioselective Total Synthesis of (+)-Flavisiamine F via Late-Stage Visible-Light-Induced Photochemical Cyclization
	Tong, Xiaogang 1,2; Shi, Bingfei 1; Liang, Kangjiang 1; Liu, Qian 1; Xia, Chengfeng 1,2
通讯作者	Xia, Chengfeng(xiacf@ynu.edu.cn)
	2019-04-08
发表期刊	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
ISSN	1433-7851
卷号	58 期号:16 页码:5443-5446
摘要	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.
关键词	alkaloids asymmetric catalysis photochemical cyclization rearrangement total synthesis
DOI	10.1002/anie.201901241
收录类别	SCI
语种	英语
WOS记录号	WOS:000463975300049
引用统计
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/67629
专题	植物化学与西部植物资源持续利用国家重点实验室
通讯作者	Xia, Chengfeng
作者单位	1.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
推荐引用方式 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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