Natural products inspired [3+2] cycloaddition enables efficient construction of hydroxylated tetrahydrofuran acetals and concise syntheses of lignans
文献类型：期刊论文
| 作者 | Cai, Dong-Yue2,3; Shi, Weiming1; Jin, Zhao-Hui2,3; Yu, Zhi-Xiang1; Zhao, Jin-Xin3; Yue, Jian-Min2,3
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| 刊名 | SCIENCE CHINA-CHEMISTRY
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| 出版日期 | 2024-05-28 |
| 页码 | 8 |
| 关键词 | [3+2] cycloaddition transition-metal catalysis tetrahydrofuran lignans natural products |
| ISSN号 | 1674-7291 |
| DOI | 10.1007/s11426-024-1988-8 |
| 通讯作者 | Yu, Zhi-Xiang(yuzx@pku.edu.cn) ; Zhao, Jin-Xin(jxzhao@simm.ac.cn) ; Yue, Jian-Min(jmyue@simm.ac.cn) |
| 英文摘要 | Mimicking biosynthetic pathways of hongkonoids led to the development of a new Cu(I)-catalyzed [3 + 2] cycloaddition of alpha-hydroxyketone and beta-keto enol ethers, affording tetrahydrofuran acetals in a highly diastereoselective manner and 100% atom economy. Computational studies on the mechanism disclosed a concerted but asynchronous Michael addition/aldol reaction. Of the same importance, this methodology provides a practical biomimetic approach for one-step construction of the dibenzylbutyrolactol lignan backbone starting from two phenyl propane derivatives, opening up a powerful new approach for lignan synthesis, which is showcased by succinct total syntheses of two biologically important aryltetralin-type lignans, beta-apopicropodophyllin and cycloolivil. Given the mild and operationally simple conditions, the developed chemistry might have a promising prospect in potential industrial applications. |
| WOS关键词 | DISCOVERY ; CHEMISTRY |
| 资助项目 | Shanghai Pujiang Program[22PJ1415800] ; National Natural Science Foundation of China[22237007] ; National Natural Science Foundation of China[T2192972] ; Youth Innovation Promotion Association of Chinese Academy of Sciences[2022282] ; Youth Innovation Promotion Association of Chinese Academy of Sciences[SMECD2022005] ; High-Performance Computing Platform of Peking University |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:001235455200001 |
| 出版者 | SCIENCE PRESS |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/311776]  |
| 专题 | 新药研究国家重点实验室 |
| 通讯作者 | Yu, Zhi-Xiang; Zhao, Jin-Xin; Yue, Jian-Min |
| 作者单位 | 1.Peking Univ, Coll Chem, Beijing Natl Lab Mol Sci BNLMS, Key Lab Bioorgan Chem & Mol Engn,Minist Educ, Beijing 100871, Peoples R China 2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 3.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Cai, Dong-Yue,Shi, Weiming,Jin, Zhao-Hui,et al. Natural products inspired [3+2] cycloaddition enables efficient construction of hydroxylated tetrahydrofuran acetals and concise syntheses of lignans[J]. SCIENCE CHINA-CHEMISTRY,2024:8. |
| APA | Cai, Dong-Yue,Shi, Weiming,Jin, Zhao-Hui,Yu, Zhi-Xiang,Zhao, Jin-Xin,&Yue, Jian-Min.(2024).Natural products inspired [3+2] cycloaddition enables efficient construction of hydroxylated tetrahydrofuran acetals and concise syntheses of lignans.SCIENCE CHINA-CHEMISTRY,8. |
| MLA | Cai, Dong-Yue,et al."Natural products inspired [3+2] cycloaddition enables efficient construction of hydroxylated tetrahydrofuran acetals and concise syntheses of lignans".SCIENCE CHINA-CHEMISTRY (2024):8. |
入库方式： OAI收割
来源：上海药物研究所
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