The synthesis of novel 8a-aza-8a-homoery thromycin derivatives via the Beckmann rearrangement of (9Z)-erythromycin A oxime

  • Wilkening R
  • Ratcliffe R
  • Doss G
 et al. 
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Abstract

The (9E)-oxime of erythromycin A was isomerized to the (9Z)-isomer in the presence of strong base. Stereospecific Beckmann rearrangement of the (9Z)-oxime led to a series of novel 8a-aza-8a-homoerythromycin A derivs. In vitro antibacterial data is provided that shows the 8a-Me deriv. to be equally active with its positional isomer azithromycin. [on SciFinder (R)]

Author-supplied keywords

  • azahomoerythromycin A prepn bactericide
  • erythromycin A oxime isomerization
  • oxime erythromycin A stereoselective Beckmann rear

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Authors

  • Robert R Wilkening

  • Ronald W Ratcliffe

  • George A Doss

  • Kenneth F Bartizal

  • Amy Graham

  • Charmaine M Herbert

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