Biomimetic Intramolecular Diels-Alder Reaction to Construct the Tetrahydroindane Core of Elansolid A1/A2

doi:10.6023/cjoc202102021

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	Biomimetic Intramolecular Diels-Alder Reaction to Construct the Tetrahydroindane Core of Elansolid A1/A2
	Yu Qi ; Yang Shuai ; Tang Congyun ; Peng Lin ; Zuo Zhili1 ; Wang Liangliang 1
	2021
发表期刊	CHINESE JOURNAL OF ORGANIC CHEMISTRY
ISSN	0253-2786
卷号	41 期号:7 页码:2820-2830
摘要	The Elansolid A1/A2 is metabolite from the gliding bacterium Chitinophaga sanctii and shows antibiotic activity against Gram-positive bacteria. Up to now, the total synthesis of this natural product has not been reported yet due to its structure complexity, which arises from the trans-tetrahydroindane unit and (Z)-(E)-(Z) triene motif as well as a 19-member macrolactone. In this study, two new O-functionalized substrates were synthesized to undergo the biomimetic intramolecular Diels-Alder reactions (IMDA) catalyzed by a chiral phosphoric acid to build the key trans-tetrahydroindane core of Elansolid A1/A2 via a vinylic p-quinone methide intermediate. This result shows that an improved dr (1.8:1) of IMDA reaction and shorter synthetic steps could be achieved.
关键词	biomimetic synthesis Diels-Alder reaction tetrahydroindane elansolid ACID OLEFIN
DOI	10.6023/cjoc202102021
WOS记录号	WOS:000691058000026
引用统计
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/73381
专题	中国科学院昆明植物研究所
作者单位	1.Shaoyang Univ, Sch Food & Chem Engn, Shaoyang 422000, Hunan, Peoples R China 2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China
推荐引用方式 GB/T 7714	Yu Qi,Yang Shuai,Tang Congyun,et al. Biomimetic Intramolecular Diels-Alder Reaction to Construct the Tetrahydroindane Core of Elansolid A1/A2[J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY,2021,41(7):2820-2830.
APA	Yu Qi,Yang Shuai,Tang Congyun,Peng Lin,Zuo Zhili,&Wang Liangliang.(2021).Biomimetic Intramolecular Diels-Alder Reaction to Construct the Tetrahydroindane Core of Elansolid A1/A2.CHINESE JOURNAL OF ORGANIC CHEMISTRY,41(7),2820-2830.
MLA	Yu Qi,et al."Biomimetic Intramolecular Diels-Alder Reaction to Construct the Tetrahydroindane Core of Elansolid A1/A2".CHINESE JOURNAL OF ORGANIC CHEMISTRY 41.7(2021):2820-2830.

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