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DOI | 10.1038/s41467-018-05443-7 |
Ti(Oi-Pr)(4)-promoted photoenolization Diels-Alder reaction to construct polycyclic rings and its synthetic applications | |
Yang, Baochao; Lin, Kuaikuai; Shi, Yingbo; Gao, Shuanhu | |
2017-09-20 | |
发表期刊 | NATURE COMMUNICATIONS
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ISSN | 2041-1723 |
出版年 | 2017 |
卷号 | 8 |
文章类型 | Article |
语种 | 英语 |
国家 | Peoples R China |
英文摘要 | Stereoselective construction of polycyclic rings with all-carbon quaternary centers, and vicinal all-carbon quaternary stereocenters, remains a significant challenge in organic synthesis. These structures can be found in a wide range of polycyclic natural products and drug molecules. Here we report a Ti(Oi-Pr)(4)-promoted photoenolization/ Diels-Alder (PEDA) reaction to construct hydroanthracenol and related polycyclic rings bearing all-carbon quaternary centers. This photolysis proceeds under mild conditions and generates a variety of photo-cycloaddition products in good reaction efficiency and stereoselectivity (48 examples), and has been successfully used in the construction of core skeleton of oncocalyxones, tetracycline and pleurotin. It also provides a reliable method for the late-stage modification of natural products bearing enone groups, such as steroids. The total synthesis of oncocalyxone B was successfully achieved using this PEDA approach. |
领域 | 资源环境 |
收录类别 | SCI-E |
WOS记录号 | WOS:000411316500005 |
WOS关键词 | HYDROXY-O-QUINODIMETHANES ; NATURAL-PRODUCT SYNTHESIS ; PHOTOASSISTED SYNTHESIS ; ANNULATION REACTIONS ; AUXEMMA-ONCOCALYX ; ORGANIC-SYNTHESIS ; ANALOGS THEREOF ; HAMIGERANS ; PLEUROTIN ; ACID |
WOS类目 | Multidisciplinary Sciences |
WOS研究方向 | Science & Technology - Other Topics |
URL | 查看原文 |
引用统计 | |
文献类型 | 期刊论文 |
条目标识符 | http://119.78.100.173/C666/handle/2XK7JSWQ/203943 |
专题 | 资源环境科学 |
作者单位 | East China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Sch Chem & Mol Engn, 3663N Zhongshan Rd, Shanghai 200062, Peoples R China |
推荐引用方式 GB/T 7714 | Yang, Baochao,Lin, Kuaikuai,Shi, Yingbo,et al. Ti(Oi-Pr)(4)-promoted photoenolization Diels-Alder reaction to construct polycyclic rings and its synthetic applications[J]. NATURE COMMUNICATIONS,2017,8. |
APA | Yang, Baochao,Lin, Kuaikuai,Shi, Yingbo,&Gao, Shuanhu.(2017).Ti(Oi-Pr)(4)-promoted photoenolization Diels-Alder reaction to construct polycyclic rings and its synthetic applications.NATURE COMMUNICATIONS,8. |
MLA | Yang, Baochao,et al."Ti(Oi-Pr)(4)-promoted photoenolization Diels-Alder reaction to construct polycyclic rings and its synthetic applications".NATURE COMMUNICATIONS 8(2017). |
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