THE SYNTHESIS OF NOVEL 8A-AZA-8A-HOMOERYTHROMYCIN DERIVATIVES VIA THEBECKMANN REARRANGEMENT OF (9Z)-ERYTHROMYCIN A OXIME

Authors
WILKENING RR RATCLIFFE RW DOSS GA BARTIZAL KF GRAHAM AC HERBERT CM
Citation
Rr. Wilkening et al., THE SYNTHESIS OF NOVEL 8A-AZA-8A-HOMOERYTHROMYCIN DERIVATIVES VIA THEBECKMANN REARRANGEMENT OF (9Z)-ERYTHROMYCIN A OXIME, Bioorganic & medicinal chemistry letters, 3(6), 1993, pp. 1287-1292
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
3
Issue
6
Year of publication
1993
Pages
1287 - 1292
Database
ISI
SICI code
0960-894X(1993)3:6<1287:TSON8D>2.0.ZU;2-W
Abstract
The (9E)-oxime of erythromycin A (1) was isomerized to the (9Z)-isomer 2 in the presence of strong base. Stereospecific Beckmann rearrangeme nt of the (9Z)-oxime led to a series of novel 8a-aza-8a-homoerythromyc in A derivatives. In vitro data is provided that shows the 8a-methyl d erivative 10 to be equally active with its positional isomer azithromy cin.