Stereoselective synthesis of pyridinones: Application to the synthesis of (-)-barrenazines
Stereoselective synthesis of pyridinones: Application to the synthesis of (-)-barrenazines
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DOI：
10.1021/ol0609006
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发表时间：
2006-07-06
期刊：
影响因子：
5.2
通讯作者：
Charette, Andre B.
中科院分区：
文献类型：
--
作者：
Focken, Thilo;Charette, Andre B.
通过格氏试剂与4-甲氧基吡啶衍生的手性吡啶盐的亲核加成，实现了吡啶酮的立体选择性合成。将该方法应用于（-）-barrenazine A和B的快速合成。在吡啶酮系统的N-官能化和1，4-还原后，相应的α-氨基哌啶酮容易进行二聚反应，得到巴雷那嗪生物碱的六氢二吡啶并吡嗪骨架。
The stereoselective synthesis of pyridinones was accomplished by the nucleophilic addition of Grignard reagents to a chiral pyridinium salt derived from 4-methoxypyridine. This methodology was applied to an expedient synthesis of (-)-barrenazine A and B. After N-functionalization and 1,4-reduction of the pyridinone system, the corresponding alpha-amino piperidinones readily undergo dimerization to give the hexahydrodipyridinopyrazine skeleton of the barrenazine alkaloids.