Total Synthesis of (+)-Lyconadin A and Related Compounds via Oxidative C-N Bond Formation
Total Synthesis of (+)-Lyconadin A and Related Compounds via Oxidative C-N Bond Formation
复制标题
DOI：
10.1021/ja903868n
复制
发表时间：
2009-08-12
影响因子：
15
通讯作者：
Sarpong, Richmond
中科院分区：
文献类型：
--
作者：
West, Scott P.;Bisai, Alakesh;Sarpong, Richmond
碳-氮键的形成是有机合成中一种基本的键结构，对生物碱类天然产物的合成是不可或缺的。在合成结构复杂的石松生物碱Lyconadin A的背景下，我们发现了一种高效的氧化C-N键形成反应，该反应依赖于N阴离子和C负离子的结合。在我们的合成研究中积累的经验证据表明，C-N键形成过程的机制既包括极性过程，也包括自由基过程。在本文中，我们介绍了我们对这一新的C-N成键反应的研究及其在不对称全合成Lyconadin A及其相关衍生物中的应用。
The formation of carbon-nitrogen (C-N) bonds is a fundamental bond construction in organic synthesis and is indispensable for the synthesis of alkaloid natural products. In the context of the synthesis of the architecturally complex Lycopodium alkaloid lyconadin A, we have discovered a highly efficient oxidative C-N bond forming reaction that relies on the union of a nitrogen anion and a carbon anion. Empirical evidence amassed during our synthetic studies suggests that the mechanism of the C-N bond forming process encompasses polar as well as radical processes. Herein, we present our study of this novel C-N bond forming reaction and its application to the enantioselective total synthesis of lyconadin A and related derivatives.