Ishihara Jun
Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 853-8521, Japan.
Molecules. 2024 Mar 6;29(5):1187. doi: 10.3390/molecules29051187.
The synthesis of natural products with complicated architectures often requires the use of segments with functional groups that can be structurally transformed with the desired stereogenic centers. Bicyclic 𝛾-lactones have great potential as a suitable segment for natural product synthesis. However, the stereoselective construction of such functionalized bicyclic 𝛾-lactones is not as straightforward as one might expect. The template-mediated Diels-Alder reaction is one of the most powerful and versatile methods for providing bicyclic 𝛾-lactones with high regioselectivity and stereoselectivity. In this reaction, the diene is linked to the dienophile by a temporary tether, allowing the reaction to proceed efficiently, yielding a product that can be used for natural product synthesis. This review describes some important instances of the template-mediated Diels-Alder reaction and its application to the synthesis of biologically active compounds.
具有复杂结构的天然产物的合成通常需要使用带有官能团的片段，这些官能团可以在所需的立体中心进行结构转化。双环γ-内酯作为天然产物合成的合适片段具有很大的潜力。然而，这种功能化双环γ-内酯的立体选择性构建并不像人们预期的那么简单。模板介导的狄尔斯-阿尔德反应是为双环γ-内酯提供高区域选择性和立体选择性的最强大且通用的方法之一。在该反应中，二烯通过临时连接基团与亲双烯体相连，使反应能够高效进行，生成可用于天然产物合成的产物。本综述描述了模板介导的狄尔斯-阿尔德反应的一些重要实例及其在生物活性化合物合成中的应用。
