Difluorination of Furonaphthoquinones

doi:10.1021/acs.joc.7b01064

	Difluorination of Furonaphthoquinones
	Li, Jie 1; Xue, Yu 2; Fan, Zhoulong 3,4,5; Ding, Chunyong3,5 ; Zhang, Ao1,3,4,5
刊名	JOURNAL OF ORGANIC CHEMISTRY
	2017-07-21
卷号	82 期号:14 页码:7388-7393
ISSN号	0022-3263
DOI	10.1021/acs.joc.7b01064
文献子类	Article
英文摘要	An unprecedented difluorination reaction was developed based on the furonaphthoquinone skeleton of natural products tanshinones and their analogues. By using Selectfluor as the fluorinating source and H2O as the hydroxyl source, a wide range of unique polycyclic alpha,alpha-difluoro beta,beta-dihydroxyl para-quinone products were achieved with yields up to 90%. The mechanistic studies revealed that the reaction might undergo tandem multiple electrophilic and nucleophilic substitutions, as well as cleavages of C-O and C-C bonds. This approach not only provides a new method to synthesis of alpha,alpha-difluoro ketones, but also affords a series of unique chemotypes for biological activity screening.
资助项目	National Natural Science Foundation of China[81373277] ; National Natural Science Foundation of China[81402790] ; International Cooperative Program[GJHZ1622] ; Frontier Science of the Chinese Academy of Sciences[160621] ; Shanghai Commission of Science and Technology[16XD1404600] ; Shanghai Commission of Science and Technology[14431905300] ; Shanghai Commission of Science and Technology[14431900400]
WOS关键词	PRODUCT TANSHINONE IIA ; DIFLUOROMETHYL KETONES ; MEDICINAL CHEMISTRY ; SALVIA-MILTIORRHIZA ; CARBONYL-COMPOUNDS ; ACID-CHLORIDES ; PLASMEPSIN II ; DERIVATIVES ; INHIBITORS ; FLUORINE
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000406355900031
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/272560]
专题	药物化学研究室中科院受体结构与功能重点实验室新药研究国家重点实验室
通讯作者	Ding, Chunyong; Zhang, Ao
作者单位	1.ShanghaiTech Univ, Shanghai 201210, Peoples R China; 2.China Pharmaceut Univ, Dept Med Chem, Nanjing 210009, Jiangsu, Peoples R China; 3.Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China; 4.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China; 5.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
推荐引用方式 GB/T 7714	Li, Jie,Xue, Yu,Fan, Zhoulong,et al. Difluorination of Furonaphthoquinones[J]. JOURNAL OF ORGANIC CHEMISTRY,2017,82(14):7388-7393.
APA	Li, Jie,Xue, Yu,Fan, Zhoulong,Ding, Chunyong,&Zhang, Ao.(2017).Difluorination of Furonaphthoquinones.JOURNAL OF ORGANIC CHEMISTRY,82(14),7388-7393.
MLA	Li, Jie,et al."Difluorination of Furonaphthoquinones".JOURNAL OF ORGANIC CHEMISTRY 82.14(2017):7388-7393.