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Nucleophilic Aromatic Substitution—A Possible Key Step in Total Syntheses of Vancomycin
Author(s) -
Burgess Kevin,
Lim Dongyeol,
Martinez Carlos I.
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199610771
Subject(s) - ring (chemistry) , vancomycin , nucleophilic aromatic substitution , chemistry , substitution (logic) , nucleophilic substitution , stereochemistry , aromaticity , transformation (genetics) , nucleophile , combinatorial chemistry , closure (psychology) , medicinal chemistry , organic chemistry , computer science , molecule , catalysis , programming language , political science , biochemistry , biology , bacteria , genetics , staphylococcus aureus , gene , law
How one of the major obstacles to a total synthesis of vancomycin 1 , R = sugar, might be overcome has been demonstrated by Zhu et al. and others. They have used nucleophilic aromatic substitution reactions for biaryl ring formation and concomitant ring closure. Conditions for this transformation are sufficiently mild that it can be applied to form complex macrocycles like the 16‐membered rings of vancomycin.