A modular and divergent approach for the total synthesis of Elaeocarpus alkaloids
文献类型：期刊论文
| 作者 | Tian, Guang1,2; Zhang, Yi-Chi2; Qin, Chuanguang1; Wang, Jie2,3 |
| 刊名 | ORGANIC CHEMISTRY FRONTIERS
 |
| 出版日期 | 2022-11-08 |
| 页码 | 6 |
| ISSN号 | 2052-4129 |
| DOI | 10.1039/d2qo01460b |
| 通讯作者 | Qin, Chuanguang() ; Wang, Jie() |
| 英文摘要 | Herein we report a unified strategy for the divergent total synthesis of six Elaeocarpus alkaloids in 6-10 steps from commercially available materials. This modular approach relied on the rapid construction of the tetrahydrobenzopyran-4-one framework through an aldol/dehydration/oxa-Michael process to set all carbons and functional groups ready for the core construction. A key NbCl5-mediated intramolecular Mannich reaction was used to build the C ring and secure both stereoisomers existing in these natural products. Finally, a diversification was achieved through the intermediacy of thioamide, with the side chain of elaeocarfoline A/B installed by an Eschenmoser sulfide contraction/reduction sequence. |
| WOS关键词 | RECEPTOR-BINDING AFFINITY ; INDOLIZIDINE ALKALOIDS ; PYRROLIDINE ALKALOIDS ; GRANDISINE-A ; LEAVES ; SUBSTITUTION |
| 资助项目 | National Natural Science Foundation of China[22101290] ; National Natural Science Foundation of China[21572180] ; Intergovernmental Science and Technology Cooperation and Exchange Program between P. R. China and Romania[43-24-20180510] ; Chinese Academy of Sciences ; Shanghai Institute of Materia Medica |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000885554400001 |
| 出版者 | ROYAL SOC CHEMISTRY |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/304656]  |
| 专题 | 中国科学院上海药物研究所 |
| 通讯作者 | Qin, Chuanguang; Wang, Jie |
| 作者单位 | 1.Northwestern Polytech Univ, Sch Chem & Chem Engn, Dept Chem, Shanxi Key Lab Polymer Sci & Technol, Xian 710129, Peoples R China 2.Chinese Acad Sci, Shanghai Inst Mat Med, Dept Med Chem, Shanghai 201203, Peoples R China 3.Univ Chinese Acad Sci, Beijing 100049, Peoples R China |
| 推荐引用方式 GB/T 7714 | Tian, Guang,Zhang, Yi-Chi,Qin, Chuanguang,et al. A modular and divergent approach for the total synthesis of Elaeocarpus alkaloids[J]. ORGANIC CHEMISTRY FRONTIERS,2022:6. |
| APA | Tian, Guang,Zhang, Yi-Chi,Qin, Chuanguang,&Wang, Jie.(2022).A modular and divergent approach for the total synthesis of Elaeocarpus alkaloids.ORGANIC CHEMISTRY FRONTIERS,6. |
| MLA | Tian, Guang,et al."A modular and divergent approach for the total synthesis of Elaeocarpus alkaloids".ORGANIC CHEMISTRY FRONTIERS (2022):6. |
入库方式： OAI收割
来源：上海药物研究所
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