Efficient preparation of β-hydroxy aspartic acid and its derivatives  

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

机构地区：[1]State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China [2]Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, China

出　　处：《Chinese Chemical Letters》2018年第7期1113-1115,共3页中国化学快报（英文版）

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

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.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.

关 键 词：Amino acid Natural product Erythreo-β-OH-Asp Erythreo-β-OMe-Asn ANTIBIOTICS 

分 类 号：O623.736[理学—有机化学]