Unusual transformation of the 3-hydroxy-picolinoyl residue of pristinamycin I(A)

Article abstract of DOI:10.7164/antibiotics.48.676

Pristinamycin I(A) was modified in a two-step procedure to give original derivatives possessing a tricyclic nucleus (8a, 8b, 8c) or a substituted pyrrole ring (10a, 10b) in place of the natural exocyclic 3-hydroxy-picolinoyl residue. This transformation involved firstly preparation of pyridinium betaines 5 from pristinamycin I(A) and secondly a 1~3 dipolar cycloaddition between 5 and N-substituted maleimides or diethyl acetylenedicarboxylate. The compounds obtained were evaluated as antibacterial agents alone and in association with pristinamycin II(A).