Changing the Reaction Pathway of Silyl-Prins Cyclization by Switching the Lewis Acid: Application to the Synthesis of an Antinociceptive Compound,The Journal of Organic Chemistry

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Changing the Reaction Pathway of Silyl-Prins Cyclization by Switching the Lewis Acid: Application to the Synthesis of an Antinociceptive Compound
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-05-23 , DOI: 10.1021/acs.joc.3c00050
Carlos Díez-Poza ₁ , Laura Fernández-Peña ₁ , Paula González-Andrés ₁ , Asunción Barbero ₁

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Developing new procedures for the synthesis of tetrahydropyrans in a very stereoselective manner is of great importance for the synthesis of THP-containing natural products. Here, we report an interesting protocol for the synthesis of polysubstituted halogenated tetrahydropyrans by silyl-Prins cyclization of vinylsilyl alcohols, in which the nature of the Lewis acid determines the outcome of the process. The methodology has been applied to the synthesis of a known antinociceptive.

中文翻译：

通过改变路易斯酸改变甲硅烷基-普林斯环化反应途径：在镇痛化合物合成中的应用

开发以非常立体选择性的方式合成四氢吡喃的新程序对于合成含 THP 的天然产物非常重要。在这里，我们报告了一个有趣的协议，用于通过乙烯基硅醇的硅基-普林斯环化合成多取代卤化四氢吡喃，其中路易斯酸的性质决定了该过程的结果。该方法已应用于合成一种已知的镇痛药。

更新日期：2023-05-23

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