南方科技大学知识苑(SUSTech KC): Total Syntheses of Calyciphylline A-Type Alkaloids (-)-10-Deoxydaphnipaxianine A, (+)-Daphlongamine E and (+)-Calyciphylline R via Late-Stage Divinyl Carbinol Rearrangements

题名	Total Syntheses of Calyciphylline A-Type Alkaloids (-)-10-Deoxydaphnipaxianine A, (+)-Daphlongamine E and (+)-Calyciphylline R via Late-Stage Divinyl Carbinol Rearrangements
作者	Zhang, Yan1,2,3,4 ; Chen, Yuye1,2,3,4 ; Song, Manrong1,2,3,4 ; Tan, Bin1,2,3,4 ; Jiang, Yujia1,2,3,4 ; Yan, Chongyuan1,2,3,4 ; Jiang, Yuyang1,2,3,4 ; Hu, Xinyue1,2,3,4 ; Zhang, Chengqian 1,2,3,4; Chen, Wenqing1,2,3,4 ; Xu, Jing1,2,3,4
通讯作者	Xu, Jing
发表日期	2022-08-01
DOI	10.1021/jacs.2c05957
发表期刊	Journal of the American Chemical Society 影响因子和分区
ISSN	0002-7863
EISSN	1520-5126
摘要	Among the famous Daphniphyllum alkaloids family, the calyciphylline A-type subfamily has triggered particular interest from the organic synthesis community in recent years. Here, we report divergent total syntheses of three calyciphylline A-type alkaloids, namely, (-)-10-deoxydaphnipaxianine A, (+)-daphlongamine E, and (+)-calyciphylline R. Our work highlights an efficient, divergent strategy via late-stage divinyl carbinol rearrangements, including an unprecedented oxidative Nazarov electrocyclization using an unfunctionalized tertiary divinyl carbinol and an unusual allylic alcohol rearrangement. A highly efficient "donor-acceptor " platinum catalyst was used for a critical nitrile hydration step. Moreover, the power of selective amide reductions has also been showcased by novel and classic tactics.
相关链接	[来源记录]
收录类别	SCI
语种	英语
重要成果	NI论文
学校署名	第一 ; 通讯
资助项目	NSFC["21971104","22001114"] ; Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis[ZDSYS20190902093215877] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002] ; Guang-dong Innovative Program[2019BT02Y335]
WOS研究方向	Chemistry
WOS类目	Chemistry, Multidisciplinary
WOS记录号	WOS:000849327700001
出版者	AMER CHEMICAL SOC
来源库	Web of Science
引用统计	被引频次[WOS]：26
成果类型	期刊论文
条目标识符	http://sustech.caswiz.com/handle/2SGJ60CL/395966
专题	理学院_化学系深圳格拉布斯研究院
作者单位	1.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Peoples R China 2.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China 3.Southern Univ Sci & Technol, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China 4.Southern Univ Sci & Technol, Shenzhen Key Lab Small Mol Drug Discovery & Synth, Shenzhen 518055, Peoples R China
第一作者单位	化学系; 深圳格拉布斯研究院; 南方科技大学
通讯作者单位	化学系; 深圳格拉布斯研究院; 南方科技大学
第一作者的第一单位	化学系
推荐引用方式 GB/T 7714	Zhang, Yan,Chen, Yuye,Song, Manrong,et al. Total Syntheses of Calyciphylline A-Type Alkaloids (-)-10-Deoxydaphnipaxianine A, (+)-Daphlongamine E and (+)-Calyciphylline R via Late-Stage Divinyl Carbinol Rearrangements[J]. Journal of the American Chemical Society,2022.
APA	Zhang, Yan.,Chen, Yuye.,Song, Manrong.,Tan, Bin.,Jiang, Yujia.,...&Xu, Jing.(2022).Total Syntheses of Calyciphylline A-Type Alkaloids (-)-10-Deoxydaphnipaxianine A, (+)-Daphlongamine E and (+)-Calyciphylline R via Late-Stage Divinyl Carbinol Rearrangements.Journal of the American Chemical Society.
MLA	Zhang, Yan,et al."Total Syntheses of Calyciphylline A-Type Alkaloids (-)-10-Deoxydaphnipaxianine A, (+)-Daphlongamine E and (+)-Calyciphylline R via Late-Stage Divinyl Carbinol Rearrangements".Journal of the American Chemical Society (2022).