Fluorine-containing amino acids and their derivatives. 4. Synthesis and antibacterial activity of threo and erythro 1-fluorodehydroxylated chloramphenicol analogues.

Both threo and erythro 1-fluorodehydroxylated chloramphenicol analogues were synthesized and tested for antimicrobial activity. None showed antibacterial or antifungal activity, clearly demonstrating that substitution of the secondary hydroxyl group with fluorine abolishes the antibacterial activity of the parent compound, chloramphenicol. This finding sharply contrasts with that of previous workers, in which fluorination of the 3-hydroxyl group enhanced antibacterial activity against many chloramphenicol-resistant strains.