Construction of the Lactone-Bridged Scaffold of Alstoscholactine through an Acid-Catalyzed Prins Cyclization/Lactonization Cascade

作者：Yaxuan Duan, Yuting Yang, Zhengyi Qin, Xinyu Liang, Zhiyu Zhang, Bowen Fang, Huilin Li, Xuegong She · 发表于：Organic Letters · 年份：2025 · DOI：10.1021/acs.orglett.5c02725 · 被引用次数：2 · 研究领域：Synthetic Organic Chemistry Methods、Chemical synthesis and alkaloids、Asymmetric Synthesis and Catalysis

Described herein is an acid-catalyzed Prins cyclization/lactonization cascade reaction of malonate-tethered inol-3-ylmethanol-olefin substrates, which rapidly constructs the lactone-bridged scaffold of the monoterpenene indole alkaloid alstoscholactine. This reaction demonstrates a wide substrate scope and functional group tolerance, and a catalytic asymmetric reaction provides high enantioselectivity. This work provides a powerful method to access the key framework of alstoscholactine and supports the proposed plausible biogenetic pathway.