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

页码：932 / 935

页数：4

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