通过酸不稳定烯醇醚的无痕固相合成酮：在天然产物和衍生物合成中的应用。

Department of Organic Chemistry, Faculty of Science, Palacký University, 17. listopadu 12, 771 46 Olomouc, Czech Republic.

Department of Chemistry and Biochemistry, 251 Nieuwland Science Center, University of Notre Dame, Notre Dame, IN 46556, USA.

Molecules. 2019 Apr 10;24(7):1406. doi: 10.3390/molecules24071406.

In solid-phase organic synthesis, Wang resin is traditionally used for the immobilization of acids, alcohols, phenols, and amines. We report the use of Wang resin for the traceless synthesis of ketones via acid-labile enol ethers. We demonstrate the practicality of this synthetic strategy on the solid-phase synthesis of pyrrolidine-2,4-diones, which represent the core structure of several natural products, including tetramic acid. Base-triggered condensation of pyrrolidine-2,4-diones yielded 4-hydroxy-1,1',2',5-tetrahydro-2,5'-[3,3'-bipyrrole]-2,5'-diones.

在固相有机合成中，Wang 树脂传统上用于固定酸、醇、酚和胺。我们报告了 Wang 树脂在通过酸不稳定烯醇醚合成酮方面的应用。我们通过固相合成吡咯烷-2,4-二酮证明了这种合成策略的实用性，吡咯烷-2,4-二酮代表了几种天然产物的核心结构，包括四氢酸。吡咯烷-2,4-二酮在碱基引发下缩合生成 4-羟基-1,1',2',5-四氢-2,5'-[3,3'-联吡啶]-2,5'-二酮。