Catalyst-Free sp(3) C-H Acyloxylation: Regioselective Synthesis of 1-Acyloxy Derivatives of the Natural Product Tanshinone IIA
文献类型：期刊论文
| 作者 | Ding, Chunyong1,3 ; Li, Jie1,2; Jiao, Mingkun1,3; Zhang, Ao1,2,3
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| 刊名 | JOURNAL OF NATURAL PRODUCTS
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| 出版日期 | 2016-10 |
| 卷号 | 79期号:10页码:2514-2520 |
| ISSN号 | 0163-3864 |
| DOI | 10.1021/acs.jnatprod.6b00370 |
| 文献子类 | Article |
| 英文摘要 | Tanshinone IIA is a valuable bioactive natural product isolated from the well-known Chinese herb Danshen. Structural manipulation of the A-ring of tanshinone IIA is rather limited. In this study, a substrate tautomerization-induced catalyst-free benzylic sp(3) C-H acyloxylation approach is reported that allows the direct introduction of various acyloxy groups at the A-ring benzylic methylene of various tanshinone IIA substrates, thus avoiding the use of expensive transition metal catalysts and the production of harmful byproducts. This approach features a unique acid-induced reversible enolization/oxa-conjugate addition process followed by oxidation to exclusively give a series of diverse 1-acyloxylated derivatives under simple conditions in a regioselective manner. Compared with the literature procedures, this protocol demonstrates a higher efficiency, a more robust functional-group tolerance, atom economy, and lower cost. |
| WOS关键词 | FREE OXIDATIVE ESTERIFICATION ; SALVIA-MILTIORRHIZA BUNGE ; VASODILATIVE ACTIVITY ; BOND ACTIVATION ; FUNCTIONALIZATION ; CYCLOALKANES ; CHEMISTRY ; ARYLATION ; ALDEHYDES ; STRATEGY |
| 资助项目 | National Natural Science Foundation of China[81402790] ; National Natural Science Foundation of China[81125021] ; National Natural Science Foundation of China[81373277] ; National Natural Science Foundation of China[81430080] ; Pujiang Talent Project from the Shanghai Commission of Science and Technology[14PJ1410700] |
| WOS研究方向 | Plant Sciences ; Pharmacology & Pharmacy |
| 语种 | 英语 |
| WOS记录号 | WOS:000386745300012 |
| 出版者 | AMER CHEMICAL SOC |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/275873]  |
| 专题 | 药物化学研究室 |
| 通讯作者 | Zhang, Ao |
| 作者单位 | 1.Chinese Acad Sci, Shanghai Inst Mat Med, Synthet Organ & Med Chem Lab, CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China; 2.ShanghaiTech Univ, Shanghai 20120, Peoples R China; 3.Univ Chinese Acad Sci, Beijing 100049, Peoples R China |
| 推荐引用方式 GB/T 7714 | Ding, Chunyong,Li, Jie,Jiao, Mingkun,et al. Catalyst-Free sp(3) C-H Acyloxylation: Regioselective Synthesis of 1-Acyloxy Derivatives of the Natural Product Tanshinone IIA[J]. JOURNAL OF NATURAL PRODUCTS,2016,79(10):2514-2520. |
| APA | Ding, Chunyong,Li, Jie,Jiao, Mingkun,&Zhang, Ao.(2016).Catalyst-Free sp(3) C-H Acyloxylation: Regioselective Synthesis of 1-Acyloxy Derivatives of the Natural Product Tanshinone IIA.JOURNAL OF NATURAL PRODUCTS,79(10),2514-2520. |
| MLA | Ding, Chunyong,et al."Catalyst-Free sp(3) C-H Acyloxylation: Regioselective Synthesis of 1-Acyloxy Derivatives of the Natural Product Tanshinone IIA".JOURNAL OF NATURAL PRODUCTS 79.10(2016):2514-2520. |
入库方式： OAI收割
来源：上海药物研究所
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