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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201501890
Subject(s) - glycosylation , total synthesis , aldol reaction , chemistry , stereoselectivity , acylation , acetal , nucleoside , stereochemistry , intramolecular force , combinatorial chemistry , biochemistry , catalysis
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.