Chemoselective synthesis of erythromycin A ketolides substituted in the C10-methyl group |
| |
Authors: | Gunnes Sølvi Undheim Kjell |
| |
Institution: | Department of Chemistry, University of Oslo, N-0315 Oslo, Norway. |
| |
Abstract: | The substrate for selective substitution in the C10-methyl group in erythromycin A derivatives was 10,11-anhydro-6O-methyl-descladinosylerythromycin. The latter, as an N-oxide, was reacted with NBS in acetic acid to form an allylic acetate. Nucleophilic substitutions and carbylation by Pd-catalysed cross-coupling reactions provided products substituted in the C10-methyl group. Methods for the preparation of 10-methylene derivatives of 11N,12O-cyclocarbamate 3-ketolides are described. The methylene group is part of an alpha,beta-unsaturated carbonyl system involving the 9-keto group. The products from conjugated addition are substituted in the C10-methyl group. |
| |
Keywords: | |
本文献已被 ScienceDirect PubMed 等数据库收录! |
|