Formal synthesis of (+)-Brefeldin A: Application of a zinc-mediated ring expansion reaction
Formal synthesis of (+)-Brefeldin A: Application of a zinc-mediated ring expansion reaction
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DOI：
10.1021/jo0701379
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发表时间：
2007-06-08
影响因子：
3.6
通讯作者：
Zercher, Charles K.
中科院分区：
文献类型：
--
作者：
Lin, Weimin;Zercher, Charles K.
通过依赖于三个关键步骤的合成方法完成了（+）-布雷菲德菌素A的有效形式合成。通过应用Toru开发的串联共轭加成-分子内环化方法以立体控制的方式生成五元环。闭环复分解提供了获得十二元β-酮内酯的途径，其通过类卡宾锌介导的反应扩环为α，β-不饱和-γ-酮内酯。先前已经报道了这种内酯转化为（+）-布雷菲德菌素A。
An efficient formal synthesis of (+)-brefeldin A was accomplished through a synthetic approach that relied upon three keys steps. The five-membered ring was generated in a stereocontrolled fashion through application of a tandem conjugate addition-intramolecular cyclization method developed by Toru. Ring-closing metathesis provided access to a twelve-membered beta-keto lactone, which was ring-expanded to the alpha,beta-unsaturated-gamma-keto lactone through a zinc carbenoid-mediated reaction. Conversion of this lactone to (+)-brefeldin A has been reported previously.