A Modular Approach to the Total Synthesis of Tunicamycins1. (14th April 2015)

• Record Type: Journal Article
• Authors: Li, Jiakun; Yu, Biao
• Is Part Of: Angewandte Chemie. Volume 127:Number 22(2015)
• Page Start: 6718
• Page End: 6721
• Publication Date: 2015-04-14
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201501890
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The tunicamycins constitute a delicate mimic of the bisubstrate intermediates of <italic>N</italic>‐acetyl‐<sc>D</sc>‐hexosamine‐1‐phosphate translocases and thus inhibit bacterial cell‐wall synthesis and the N glycosylation 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 N glycosylation, and final N acylation were used as the key steps.</p> </abstract>