Application of aryl siloxane cross-coupling to the synthesis of allocolchicinoids.
Application of aryl siloxane cross-coupling to the synthesis of allocolchicinoids.
复制标题
DOI：
10.1021/ol061413t
复制
发表时间：
2006-08
期刊：
影响因子：
5.2
通讯作者：
Seganish Wm;P. DeShong
中科院分区：
文献类型：
--
作者：
Seganish Wm;P. DeShong
在本次通讯中，我们报告了一种基于芳基硅氧烷偶联反应和菲酚环扩展的同种秋水仙碱碳环骨架的新方法。这些关键步骤允许对碳环框架内的每个碳进行选择性官能化。硅氧烷偶联-菲酚序列被应用于合成两种别秋水仙素类化合物，包括第一个完全合成 N-乙酰秋水仙酚-O-甲基醚 (NCME) 的方法。
In this communication, we report a new approach to the allocolchicine carbocyclic skeleton based upon an aryl siloxane coupling reaction and a phenanthrol ring expansion. These key steps allow for the selective functionalization of every carbon within the carbocyclic framework. The siloxane coupling-phenanthrol sequence was applied to the synthesis of two allocolchicinoids, including the first fully synthetic approach to N-acetyl colchinol-O-methyl ether (NCME).