Protecting-Group-Free Total Synthesis of (-)-Pallambins A—D

• 作者: Xiwu Zhang Yuan Wang Peng Chen Xinxian Cai Yanxing Jia
• 来源期刊: 中国化学（英文版）
• 年，卷（期）: 2021,（7）
• 所属期刊栏目: Comprehensive Reports
• 页码范围: 1983-1996
• 页数: 14页
• 语种: 英文
• DOI: 10.1002/cjoc.202100001

摘要

Main observation and conclusion A full account of the total synthesis of (-)-pallambins A—D (1-6) is described.The strategy was devised by simulating their biosyn-thetic pathway.The left-part bicyclo[3.2.1]octane system of pallambins C and D was efficiently constructed via a palladium-catalyzed oxidative cyclization.For construction of the right-part tetrahydrofuran/y-lactone moiety (C/D rings),initial attempts to synthesize the allylic alcohol 15 for an one-step Pd-mediated alkoxycarbonylation have failed.However,during the course of this work,an unprece-dented CH3Li-mediated method for conversion of bromoisoxazoline to the corresponding β-hydroxy nitrile has been discovered.