关于全合成不寻常的桥连四环石松生物碱lycopladine H的探索性研究。
Exploratory studies towards a total synthesis of the unusual bridged tetracyclic Lycopodium alkaloid lycopladine H.
作者信息
Sacher Joshua R, Weinreb Steven M
机构信息
Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania, 16802, United States.
出版信息
Tetrahedron. 2011 Dec 30;67(52):10203-10207. doi: 10.1016/j.tet.2011.04.016.
Abstract
A strategy for a total synthesis of the structurally novel Lycopodium 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.
摘要
一种用于全合成结构新颖的石松生物碱lycopladine H的策略已被研究。已测试的关键步骤包括：1. 硝基乙烯与邻醌缩酮的区域选择性狄尔斯-阿尔德环加成反应，以生成生物碱的双环[2.2.2]辛烷部分；2. 立体选择性亨利反应，以在C-5处产生所需的官能团和构型；3. 三取代烯烃的立体选择性催化氢化反应，以确定C-15甲基的构型。
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