Huang Yifei, Tan Mengting, Wang Nengzhong, Zhang Yufei, Yao Hui, Xiao Xiao, Huang Nianyu, Zou Kun
Hubei Key Laboratory of Natural Products Research and Development, Key Laboratory of Functional Yeast (China National Light Industry), College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, China.
Institute of Pharmaceutical Science and Technology, Zhejiang University of Technology, Hangzhou 310014, China.
J Org Chem. 2023 Sep 15;88(18):13030-13041. doi: 10.1021/acs.joc.3c01154. Epub 2023 Aug 30.
A novel highly regio- and diastereoselective phosphine-catalyzed [2 + 4] annulation of benzofuran-derived azadienes (BDAs) with acidic hydrogen-tethered allyl carbonates has been developed ingeniously. A range of functionalized spiro[benzofuran-cyclohexane] derivatives with two consecutive stereocenters were smoothly obtained in moderate to excellent yields under mild reaction conditions from readily available materials. Moreover, this method is a practical and scalable strategy that creates the core structural motif of the fungistatic drug, griseofulvin.
一种新颖的、高度区域和非对映选择性的膦催化苯并呋喃衍生的氮杂二烯（BDAs）与酸性氢连接的烯丙基碳酸酯的[2 + 4]环化反应已被巧妙地开发出来。在温和的反应条件下，从容易获得的原料中以中等至优异的产率顺利得到了一系列具有两个连续立体中心的功能化螺[苯并呋喃-环己烷]衍生物。此外，该方法是一种实用且可扩展的策略，可构建抑菌药物灰黄霉素的核心结构基序。
