Nucleophilic Aromatic Substitution—A Possible Key Step in Total Syntheses of Vancomycin

4-Nitrophenyltriflate and 4-Nitrophenylnonaflate as New Perfluoroalkanesulfonyl Transfer Agents: Experimental and Computational Studies

“…In connection with our ongoing research in the field of nucleophilic aromatic substitution reactions (S N Ar), we had the occasion to study the reaction of o- and p- nitro-substituted phenyl triflate and nonaflate with phenols. We wish to report in this paper that 4-nitrophenyl triflate ( 1 ) and 4-nitrophenyl nonaflate ( 2 ) are efficient perfluoroalkanesulfonyl transfer agents under very mild conditions. , …”

Post-assembly Peptide Modifications by Chemical Methods

“…Vancomycin, a peptide-based antibiotic drug has gained immense attention and studies directed towards its synthesis via cross-coupling reaction and other strategies are summarized in the recent review [18]. Evans and co-workers have synthesized the macrocyclic actinoidinic-containing vancomycin subunit using the oxidative coupling of arylglycine-containing peptides (Scheme 13) [19].…”

Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

“…The biogenetic importance of biaryl erythrina alkaloids may be seen by the fact that some of them have been found to act as intermediates in the biosynthesis of tetracyclic homoerythrina alkaloids (1 294). [1296][1297][1298][1299][1300][1301][1302][1303][1304][1305][1306][1307][1308][1309], which succeeded only a short time ago when the two first synthetic pathways to vancomycin (9) (1310) and its aglycone (1311)(1312)(1313)(1314)(1315)(1316) were developed, nearly simultaneously. This key biaryl intermediate 600 is further transformed into erythraline (601), as has been deduced from feeding experiments using (S)-[l-13 C]-norreticuline (599).…”