Chemistry and Structure of Ganefromycin.

Ganefromycins are antibiotics produced by Streptomyces lydicus sp. tanzanius having commercial potential as performance enhancement agents for livestock. Ganefromycins are related to the elfamycin family of antibiotics but contain several unique chemical features which are the source of novel and unexpected chemistry. Reactions under mildly basic conditions resulted in the interconversion of ganefromycins α (1) and β (2) by a 1,2-acyl migration. Strong bare causes elimination of a trisaccharide whose structure war solved by single-crystal X-ray diffraction analysis of the triacetate of the reduced ring-opened triol. Ammonolysis yields the same rearranged product from either 1 or 2