Efficient preparation of β-hydroxy aspartic acid and its derivatives
Efficient preparation of β-hydroxy aspartic acid and its derivatives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.