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

TETRAHEDRON

卷:67

Article

Sacher, Joshua R.¹  Weinreb, Steven M.¹ 

[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA

关键词: Natural product;    Alkaloid;    Diels-Alder;    Henry reaction;    Catalytic hydrogenation;   

DOI  :  10.1016/j.tet.2011.04.016

来源: Elsevier

【 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.

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