Exploratory studies towards a total synthesis of the unusual bridged tetracyclic Lycopodium alkaloid lycopladine H

被引：7
|
作者：
Sacher, Joshua R. [1 ]
Weinreb, Steven M. [1 ]
机构：
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
来源：
TETRAHEDRON | 2011年 / 67卷 / 52期
基金：
美国国家科学基金会;
关键词：
Natural product; Alkaloid; Diels-Alder; Henry reaction; Catalytic hydrogenation; MASKED O-BENZOQUINONES; DIELS-ALDER REACTIONS; ANTICAPSIN;
D O I：
10.1016/j.tet.2011.04.016
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A strategy for a total synthesis of the structurally novel Lyco podium alkaloid lycopladine H has been investigated. Key steps that have been tested include: 1. a regioselective Diels-Alder cycloaddition of nitroethylene with an o-quinone ketal to produce the bicyclo[2.2.2]octane moiety of the alkaloid; 2. a stereoselective Henry reaction to generate the requisite functionality and configuration at C-5; 3. a stereoselective catalytic hydrogenation of a trisubstituted alkene to set the C-15 methyl configuration. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：10203 / 10207
页数：5
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