Total synthesis and stereochemistry establishmentof tumescenamide A

作     者：Hong Xue Shiming Fan Jingzhe Xu Shouxin Liu 

作者机构：College of ScienceYanbian UniversityYanji133002China College of Chemical&Pharmaceutical EngineeringHebei University of Science&TechnologyShijiazhuang050018China 

出 版 物：《Organic Chemistry Frontiers》 (有机化学前沿（英文）)

年 卷 期：2022年第9卷第6期

页      面：1675-1679页

核心收录：

学科分类：07[理学] 070303[理学-有机化学] 0703[理学-化学] 

基　　金：The authors are grateful for the financial assistance received from the Basic Research Program of China(No.2010CB512007 and 2012CB723501) the National Natural Science Foundation of China(No.30472074,30873139,21978076) Hebei Provincial Natural Science Foundation of China(No.H2020208030). 

主　　题：synthesis stereochemistry elimination 

摘      要：Tumescenamide A (1), isolated from Streptomyces tumescens YM23-20, consists of a cyclic depsipeptideand a side-chain 2,4-dimethylheptanoate (Dmh). Herein, we report the first total synthesis of tumescenamide A (1) and establish its stereochemistry. The configuration of Dmh is 2S,4S and, notably, the configuration of Val is revised as D. In addition, a mild and practical method for the β-elimination of derivatives ofserine and threonine by using nano-K_(2)CO_(3) as a base was established. A highly stereoselective synthesis ofthe Dmh substructure was also developed.