A Modular Approach to the Total Synthesis of Tunicamycins
A Modular Approach to the Total Synthesis of Tunicamycins
复制标题
衣霉素全合成的模块化方法
DOI：
10.1002/anie.201501890
复制
发表时间：
2015-05-26
影响因子：
16.6
通讯作者：
Yu, Biao
中科院分区：
文献类型：
--
作者：
Li, Jiakun;Yu, Biao
tunicamyins是n -乙酰- d -己糖胺-1-磷酸转座酶的二基质中间体的精细模拟物，从而抑制细菌细胞壁合成和真核蛋白的糖基化。现在报道了一种合成这种独特类型核苷类抗生素的有效方法，其特点是以高度立体选择性和稳健的方式组装五个模块。以Mukaiyama醛醇反应、分子内缩醛形成、金(I)催化的O和n糖基化以及最终的酰化为关键步骤。
The tunicamycins constitute a delicate mimic of the bisubstrate intermediates of N-acetyl-D-hexosamine-1-phosphate translocases and thus inhibit bacterial cell-wall synthesis and the Nglycosylation of eukaryotic proteins. An efficient approach to the synthesis of this unique type of nucleoside antibiotics is now reported and features the assembly of five modules in a highly stereoselective and robust manner. A Mukaiyama aldol reaction, intramolecular acetal formation, gold(I)-catalyzed O and Nglycosylation, and final Nacylation were used as the key steps.