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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...
A method for chemical modifications of the relatively unreactive C10-methyl group in the erythromycin macrolactone ring has been developed. Erythralosamine was protected as an N-oxide in the N,N-dimethylamino group and reacted with NBS in acetic acid to provide two regioisomeric allylic bromides. The same amine was formed from both isomers on nucleophilic substitution. Both regioisomeric bromides...
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