Synthesis of CBD and Its Derivatives Bearing Various C4 '-Side Chains with a Late-Stage Diversification Method
文献类型：期刊论文
| 作者 | Gong, Xudong2,3; Sun, Changliang4; Abame, Melkamu Alemu1; Shi, Wenqiang1; Xie, Yuanchao1; Xu, Wanbin1; Zhu, Fuqiang4; Zhang, Yan1; Shen, Jingshan1 ; Aisa, Haji A.2
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| 刊名 | JOURNAL OF ORGANIC CHEMISTRY
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| 出版日期 | 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. |
| WOS关键词 | SUZUKI-MIYAURA ; SIDE-CHAIN ; CANNABIDIOL ; NEGISHI ; CANNABINOIDS ; COUPLINGS ; ANALOG ; ACID |
| 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研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000516665800084 |
| 出版者 | AMER CHEMICAL SOC |
| 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.Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai, Peoples R China 2.Chinese Acad Sci, Xinjiang Tech Inst Phys & Chem, Urumqi, Peoples R China 3.Univ Chinese Acad Sci, Beijing, 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. |
入库方式： OAI收割
来源：上海药物研究所
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