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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 Liangliang1
2021
发表期刊CHINESE JOURNAL OF ORGANIC CHEMISTRY
ISSN0253-2786
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
DOI10.6023/cjoc202102021
WOS记录号WOS:000691058000026
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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
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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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文件名: 157-I19-Chin. J. Org. Chem. 2021, 41, 2820.pdf
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