Highly stereoselective and modular syntheses of 10-hydroxytrilobacin and three diastereomers via stereodivergent [3+2]-annulation reactions
Highly stereoselective and modular syntheses of 10-hydroxytrilobacin and three diastereomers via stereodivergent [3+2]-annulation reactions
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DOI：
10.1021/ol801242d
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发表时间：
2008-08-07
期刊：
影响因子：
5.2
通讯作者：
Roush, William R.
中科院分区：
文献类型：
--
作者：
Huh, Chan Woo;Roush, William R.
以四氢呋喃甲醛2a和烯丙基硅烷3为原料，通过[3 + 2]成环反应合成了番荔枝内酯10-羟基三叶草素（4a）。[3 + 2]-成环反应的立体分散性使得有可能通过使用简单的反应条件修改从相同的前体实现三种10-羟基trilobacin非对映体的模块化、高度立体选择性合成。
A convergent synthesis of the annonaceous acetogenin, 10-hydroxytrilobacin (4a), was accomplished by using the [3 + 2]-annulation reaction of tetrahydrofuranyl carboxaldehyde 2a and allylsilane 3. The stereodivergency of the [3 + 2]-annulation reaction made it possible to achieve modular, highly stereoselective syntheses of three 10-hydroxytrilobacin diastereomers from the same precursors by using simple modifications of reaction conditions.