| A concise formal stereoselective total synthesis of （-）-swainsonine |
| |
| 引用本文： | Xiao-Gang Wang,Ai-E Wang,Pei-Qiang Huang. A concise formal stereoselective total synthesis of （-）-swainsonine[J]. 中国化学快报, 2014, 25(2): 193-196. DOI: 10.1016/j.cclet.2013.12.003 |
| |
| 作者姓名： | Xiao-Gang Wang Ai-E Wang Pei-Qiang Huang |
| |
| 作者单位： | [1]Department of Chemistry, College of Chemistry and Chemical Engineering, and Fujian Provincial Key Laboratory of Chemical Biology, Xiamen University, Xiamen 361005, China [2]State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China |
| |
| 基金项目： | The authors are grateful for financial support from the National Basic Research Program （973 Program） of China （No. 2010CB833200）, the NSF of China （Nos. 21332007, 21072160）, and the Program for Changjiang Scholars and Innovative Research Team in University （PCSIRT） of Ministry of Education, China for financial support. |
| |
| 摘 要： | A short formal stereoselective synthesis of （-）-swainsonine （1） is described. Our synthesis started with the versatile building block （R）-3-benzyloxyglutarimide 5. Through controlled regioselective reduction, Ley＇s-sulfone chemistry （N-α-sulfonylation and ZnCl2-catalyzed N-α-amidovinylation）, an RCM reaction, and an amide reduction, the synthesis of unsaturated indolizidine （8R,8aS）-3 has been achieved in five steps. The indolizidine （8R,8aS）-3 is an advanced intermediate toward the synthesis of （-）-swainsonine （1）.
|
| 关 键 词： | 立体选择性合成 苦马豆素 全合成 简洁 选择性还原 控制区域 氯化锌 磺酰化 |
| 收稿时间： | 2013-08-28 |
| 修稿时间： | 2013-11-08 |
A concise formal stereoselective total synthesis of (—)-swainsonine |
| |
| Xiao-Gang Wang,Ai-E Wang,Pei-Qiang Huang. A concise formal stereoselective total synthesis of (—)-swainsonine[J]. Chinese Chemical Letters, 2014, 25(2): 193-196. DOI: 10.1016/j.cclet.2013.12.003 |
| |
| Authors: | Xiao-Gang Wang Ai-E Wang Pei-Qiang Huang |
| |
| Affiliation: | a Department of Chemistry, College of Chemistry and Chemical Engineering, and Fujian Provincial Key Laboratory of Chemical Biology, Xiamen University,Xiamen 361005, China;b State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China |
| |
| Abstract: | A short formal stereoselective synthesis of (—)-swainsonine (1) is described. Our synthesis started with the versatile building block (R)-3-benzyloxyglutarimide 5. Through controlled regioselective reduction, Ley's-sulfone chemistry (N-α-sulfonylation and ZnCl2-catalyzed N-α-amidovinylation), an RCM reaction, and an amide reduction, the synthesis of unsaturated indolizidine (8R,8aS)-3 has been achieved in five steps. The indolizidine (8R,8aS)-3 is an advanced intermediate toward the synthesis of (—)-swainsonine (1). |
| |
| Keywords: | Indolizidines Alkaloids &alpha -Amidoalkylation Building blocks Stereoselective synthesis |
| 本文献已被 维普 ScienceDirect 等数据库收录！ |
| 点击此处可从《中国化学快报》浏览原始摘要信息 |
|
点击此处可从《中国化学快报》下载全文 |
|
