76820-32-1Relevant articles and documents
Erythromycin Series. Part 11. Ring Expansion of Erythromycin A Oxime by the Beckmann Rearrangement
Djokic, Slobodan,Kobrehel, Gabrijela,Lazarevski, Gorjana,Lopotar, Nevenka,Tamburasev, Zrinka,et al.
, p. 1881 - 1890 (2007/10/02)
The synthesis of 10-dihydro-10-deoxo-11-azaerythromycin A (11) by the Beckmann rearrangement of erythromycin A oxime (2) and reduction of the imino ether so obtained (5) is described.The structure elucidation of the new ring-expanded semisynthetic erythromycins (5) and (11) has been established on the basis of their analytical and spectral data and acid-catalysed degradation into the aglycones (7) and (13), respectively.Finally, the complete structure of ring-expanded erythronolides (7) and (13) has been determined by X-ray crystallography.