Erythromycin series. Part 11. Ring expansion of erythromycin A oxime by the Beckmann rearrangement
- 31 December 1985
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 11,p. 1881-1890
- https://doi.org/10.1039/p19860001881
Abstract
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.This publication has 5 references indexed in Scilit:
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