Efficient preparation of β-hydroxy aspartic acid and its derivatives

作     者：Long Liu Bo Wang Cheng Bi Gang He Gong Chen 

作者机构：State Key Laboratory and Institute of Elemento-Organic Chemistry College of Chemistry Nankai University Tianjin 300071 China Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) Tianjin 300071 China 

出 版 物：《Chinese Chemical Letters》 (中国化学快报（英文版）)

年 卷 期：2018年第29卷第7期

页      面：1113-1115页

核心收录：

学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学] 

基　　金：the National Natural Science Foundation of China(Nos. 21421062  21672105  91753124) for financial support of this work 

主　　题：Amino acid Natural product Erythreo-β-OH-Asp Erythreo-β-OMe-Asn Antibiotics 

摘      要：We report an efficient and practical synthetic route to various properly-protected erythreo-β-OH-Asp compounds, which are key β-branched a-amino acid units in coralmycin A and other peptide natural products. Fmoc and cyclic ketal-protected erythreo-β-OH-Asp 7 is prepared from cheap chiral precursor L-diethyl tortrate in six steps without the need of column purification. The modified form of 7 serves as a versatile precursor to various β-alkoxyl analogs of erythreo-β-OH-Asp. In addition, we successfully performed a model study toward the total synthesis of coralmycin A, featuring a late stage installation of the side chain primary amide group of erythreo-β-OMe-Asn.