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

doi:10.1002/asia.202300063

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	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
	Xu,Wenqiang; Sun,Tian-Yu; Di,Yingtong; Hao,Xiaojiang; Wu,Yun-Dong
	2023
发表期刊	CHEMISTRY-AN ASIAN JOURNAL
ISSN	1861-471X
卷号	18 期号:7
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.
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
学科领域	Chemistry
DOI	10.1002/asia.202300063
收录类别	SCI
WOS记录号	WOS:000940241700001
引用统计
文献类型	期刊论文
条目标识符	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).

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