Biomimetic Intramolecular Diels-Alder Reaction to Construct the Tetrahydroindane Core of Elansolid A1/A2
文献类型：期刊论文
| 作者 | Yu Qi; Yang Shuai; Tang Congyun; Peng Lin; Zuo Zhili1 ; Wang Liangliang1
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| 刊名 | CHINESE JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2021 |
| 卷号 | 41期号:7页码:2820-2830 |
| 关键词 | biomimetic synthesis Diels-Alder reaction tetrahydroindane elansolid ACID OLEFIN |
| ISSN号 | 0253-2786 |
| DOI | 10.6023/cjoc202102021 |
| 英文摘要 | 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. |
| WOS记录号 | WOS:000691058000026 |
| 源URL | [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. |
入库方式： OAI收割
来源：昆明植物研究所
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