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A Modular Approach to the Total Synthesis of Tunicamycins
Author(s) -
Li Jiakun,
Yu Biao
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201501890
Subject(s) - glycosylation , chemistry , aldol reaction , total synthesis , stereoselectivity , acetal , acylation , nucleoside , stereochemistry , intramolecular force , combinatorial chemistry , catalysis , biochemistry
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 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.