Furanomycin Derivatives

In 1967 Katagiri et al. observed that metabolites of the fungus Streptomyces threomy­ceticus L-803 inhibit the growing of Coliphage T2. The active compound was isolated from the fermentation broth and was called furanomycin.

  • K. Katagiri, K. Tori, Y. Kimura, T. Yoshida, T. Nagasaki, H. Minato, J. Med. Chem. 1967, 10, 1149–1154.

Several types of furanomycin analogues were synthesized and investigated with respect to their antibac­terial activity. Two different synthetic pathways were developed, based on aldol reactions/ring closing metathesis and an ester enolate Claisen rearrangement. Only the natural product and its desmethyl derivative showed antibacterial activity, pointing towards a narrow structure activity relationship.

  • U. Kazmaier, S. Pähler, R. Endermann, D. Häbich, H.-P. Kroll, B. Riedl, "Straigtforward Syntheses of Furanomycin Derivatives and their Biological Evaluation", Bioorg. Med. Chem. 2002, 10, 3905–3913.