A concise formal stereoselective total synthesis of (-)-swainsonine

被引：26
|
作者：
Wang, Xiao-Gang [1 ,2 ]
Wang, Ai-E [1 ,2 ,3 ]
Huang, Pei-Qiang [1 ,2 ,3 ]
机构：
[1] Xiamen Univ, Dept Chem, Coll Chem & Chem Engn, Xiamen 361005, Peoples R China
[2] Xiamen Univ, Fujian Prov Key Lab Chem Biol, Xiamen 361005, Peoples R China
[3] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
来源：
CHINESE CHEMICAL LETTERS | 2014年 / 25卷 / 02期
关键词：
Indolizidines; Alkaloids; alpha-Amidoalkylation; Building blocks; Stereoselective synthesis; RING-CLOSING METATHESIS; INTERMOLECULAR ADDITION-REACTIONS; ASYMMETRIC-SYNTHESIS; SWAINSONINE; ALKALOIDS; IONS; (+)-SWAINSONINE; TRANSFORMATION; DERIVATIVES; ALKYLATION;
D O I：
10.1016/j.cclet.2013.12.003
中图分类号：
O6 [化学];
学科分类号：
0703 ;
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-alpha-sulfonylation and ZnCl2-catalyzed N-alpha-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). (C) 2013 Pei-Qiang Huang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
引用
收藏
页码：193 / 196
页数：4
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