The first examples of SNAr-based macrocyclization: synthesis of model carboxylate-binding pockets of vancomycin

Model carboxylate-binding pocket C-O-D rings of vancomycin and related glycopeptides were efficiently synthesized by intramol. SNAr reactions. Thus, treatment of precursors I (R = H, 4-HOC6H4) with K2CO3 in DMF gave cyclic diaryl ethers II (R1 = NO2), with II (R = 4-HOC6H4) being a mixt. of atropisomers. II (R = H, R1 = NO2) was further converted into II (R = H, R1 = NH2, H, Cl). [on SciFinder (R)]