Synthesis of CBD and Its Derivatives Bearing Various C4 '-Side Chains with a Late-Stage Diversification Method

doi:10.1021/acs.joc.9b02880

	Synthesis of CBD and Its Derivatives Bearing Various C4 '-Side Chains with a Late-Stage Diversification Method
	Gong, Xudong 1,3; Sun, Changliang 4; Abame, Melkamu Alemu 2; Shi, Wenqiang 2; Xie, Yuanchao 2; Xu, Wanbin 2; Zhu, Fuqiang 4; Zhang, Yan 2; Shen, Jingshan 2; Aisa, Haji A.3
刊名	JOURNAL OF ORGANIC CHEMISTRY
	2020-02-21
卷号	85 期号:4 页码:2704-2715
ISSN号	0022-3263
DOI	10.1021/acs.joc.9b02880
通讯作者	Shen, Jingshan(shenjingshan@simm.ac.cn) ; Aisa, Haji A.(haji@ms.xjb.ac.cn)
英文摘要	A novel synthetic route for making (-)-CBD and its derivatives bearing various C4'-side chains is developed by a late-stage diversification method. Starting from commercially available phloroglucinol, the key intermediate (-)-CBD-2OPiv-OTf is efficiently and regioselectively prepared and further undergoes Negishi cross-coupling to furnish (-)-CBD. This approach allowed an efficient synthesis of (-)-CBD in a five-step total 52% yield on a 10 g scale. Furthermore, diversification on the C4'-side chain with this method can be realized in a wide range.
资助项目	National Science Foundation for Young Scientists of China[81703338] ; National Natural Science Foundation of China[U1703235] ; National Science & Technology Major Project Key New Drug Creation and Manufacturing Program, China[2018ZX09711002] ; Central Asian Drug Discovery and Development Center of the Chinese Academy of Sciences
WOS关键词	SUZUKI-MIYAURA ; SIDE-CHAIN ; CANNABIDIOL ; NEGISHI ; CANNABINOIDS ; COUPLINGS ; ANALOG ; ACID
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000516665800084
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/280845]
专题	中国科学院上海药物研究所
通讯作者	Shen, Jingshan; Aisa, Haji A.
作者单位	1.Univ Chinese Acad Sci, Beijing, Peoples R China 2.Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai, Peoples R China 3.Chinese Acad Sci, Xinjiang Tech Inst Phys & Chem, Urumqi, Peoples R China 4.Topharman Shanghai Co Ltd, Shanghai, Peoples R China
推荐引用方式 GB/T 7714	Gong, Xudong,Sun, Changliang,Abame, Melkamu Alemu,et al. Synthesis of CBD and Its Derivatives Bearing Various C4 '-Side Chains with a Late-Stage Diversification Method[J]. JOURNAL OF ORGANIC CHEMISTRY,2020,85(4):2704-2715.
APA	Gong, Xudong.,Sun, Changliang.,Abame, Melkamu Alemu.,Shi, Wenqiang.,Xie, Yuanchao.,...&Aisa, Haji A..(2020).Synthesis of CBD and Its Derivatives Bearing Various C4 '-Side Chains with a Late-Stage Diversification Method.JOURNAL OF ORGANIC CHEMISTRY,85(4),2704-2715.
MLA	Gong, Xudong,et al."Synthesis of CBD and Its Derivatives Bearing Various C4 '-Side Chains with a Late-Stage Diversification Method".JOURNAL OF ORGANIC CHEMISTRY 85.4(2020):2704-2715.