Inverse Electron-Demanding Diels-Alder Reactions in the Chemical Synthesis of Prenylated Indole Alkaloids Containing a Bicycle[2.2.2]diazaoctane Moiety: A Theoretical Study
文献类型：期刊论文
| 作者 | Xu,Wenqiang; Sun,Tian-Yu; Di,Yingtong ; Hao,Xiaojiang; Wu,Yun-Dong
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| 刊名 | CHEMISTRY-AN ASIAN JOURNAL
 |
| 出版日期 | 2023 |
| 卷号 | 18期号:7 |
| 关键词 | alkaloids chemical synthesis inverse-electron demanding Diels-Alder reaction reaction mechanisms theoretical study BIOMIMETIC TOTAL-SYNTHESIS CORRELATED MOLECULAR CALCULATIONS MARINE-DERIVED FUNGUS GAUSSIAN-BASIS SETS (-)-VERSICOLAMIDE B ORBITAL METHODS BREVIANAMIDE-A STEPHACIDIN-A MODEL CONCISE |
| ISSN号 | 1861-471X |
| DOI | 10.1002/asia.202300063 |
| 英文摘要 | The Diels-Alder reaction is believed to be a key step in the biosynthesis of prenylated indole alkaloids containing a bicycle[2.2.2]diazaoctane moiety. Many chemical syntheses of bicyclic structures by Diels-Alder reactions have been reported, but the reaction mechanism remains underexplored. We have carried out DFT calculations on both acid- and base-promoted Diels-Alder reactions in these syntheses and reveal that the reactions occur through an inverse-electron demand mechanism. We hope that the new mechanism is helpful for the mechanistic understanding of the biosynthesis of this class of important natural products. |
| 学科主题 | Chemistry |
| WOS记录号 | WOS:000940241700001 |
| 源URL | [http://ir.kib.ac.cn/handle/151853/75330]  |
| 专题 | 中国科学院昆明植物研究所 |
| 推荐引用方式 GB/T 7714 | Xu,Wenqiang,Sun,Tian-Yu,Di,Yingtong,et al. Inverse Electron-Demanding Diels-Alder Reactions in the Chemical Synthesis of Prenylated Indole Alkaloids Containing a Bicycle[2.2.2]diazaoctane Moiety: A Theoretical Study[J]. CHEMISTRY-AN ASIAN JOURNAL,2023,18(7). |
| APA | Xu,Wenqiang,Sun,Tian-Yu,Di,Yingtong,Hao,Xiaojiang,&Wu,Yun-Dong.(2023).Inverse Electron-Demanding Diels-Alder Reactions in the Chemical Synthesis of Prenylated Indole Alkaloids Containing a Bicycle[2.2.2]diazaoctane Moiety: A Theoretical Study.CHEMISTRY-AN ASIAN JOURNAL,18(7). |
| MLA | Xu,Wenqiang,et al."Inverse Electron-Demanding Diels-Alder Reactions in the Chemical Synthesis of Prenylated Indole Alkaloids Containing a Bicycle[2.2.2]diazaoctane Moiety: A Theoretical Study".CHEMISTRY-AN ASIAN JOURNAL 18.7(2023). |
入库方式： OAI收割
来源：昆明植物研究所
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