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A number of derivatives of mutalomycin (1), a naturally occurring polyether antibiotic, have been synthesized. In the desulfurization reaction of the ethylthio derivative (5) of mutalomycin (1) with Raney-nickel we observed an unusual course of the reaction, namely the introduction of a hydroxy group instead of the usual exchange against hydrogen, leading to two reaction products, mutalomycin (1) and 28-epimutalomycin (3). The structure of 3 and 2-epimutalomycin (2), both minor metabolites from the mutalomycin fermentation, were elucidated by X-ray analysis.

journal of antibiotics

2-Epimutalomycin and 28-epimutalomycin, two new polyether antibiotics from Stereptomyces mutabilis. Derivatization of mutalomycin and the structure elucidation of two minor metabolites.