Synthesis of (±)-deoxysymbioimine using an intramolecular Diels-Alder reaction with an N-alkoxycarbonyl 2,3-dihydropyridinium cation as the dienophile

被引：16
|
作者：
Snider, BB [1 ]
Che, QL [1 ]
机构：
[1] Brandeis Univ, Dept Chem, Waltham, MA 02454 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 06期
关键词：
cycloaddition; Diels-Alder reaction; heterocycles; imines;
D O I：
10.1002/anie.200503467
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Three rings: Treatment of an N-2,2,2-trichloroethoxycarbonyl (Troc)-substituted tetrahydropyridinol (1) with BF3·Et2O in CH2Cl2 gave a tricyclic adduct 2 (31 % yield) through an intramolecular Diels-Alder reaction. Reduction with zinc gave deoxysymbioimine (3), a potential antiresorptive and anti-inflammatory drug. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：932 / 935
页数：4
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