A Modular Approach to the Total Synthesis of Tunicamycins

被引：69

作者：

Li, Jiakun ^{[1
]}

Yu, Biao ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 22期

基金：

中国国家自然科学基金;

关键词：

glycosylation; gold; nucleosides; total synthesis; tunicamycin; GLYCOSYL ORTHO-ALKYNYLBENZOATES; HIGHLY STEREOSELECTIVE-SYNTHESIS; ANTIBIOTIC TUNICAMYCINS; BIOLOGICAL-ACTIVITY; STRUCTURAL ELUCIDATION; ANTIVIRAL ACTIVITY; N-GLYCOSYLATION; HERBICIDIN C; STREPTOVIRUDINS; BIOSYNTHESIS;

D O I：

10.1002/anie.201501890

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：6618 / 6621

页数：4

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