Electrochemical reduction of 4 '-demicarosyl-10-hydro-11-dehydro-11-hydroxyimino-9-carbonyl-9-nor-8a, 9seco-8a-aza-8a-homorelomycin, the novel seco compound from the class of tylosin

摘要

The electrochemical reduction of 4'-demicarosyl-10-hydro-11-dehydro-11-hydroxyimino-9-carbonyl-9-nor-8a,9seco-8a-aza-8a-homorelomycin was investigated by cyclic voltammetry and preparative scale electrolysis. It has been found that oxime group is reduced by ECEC mechanism in a four-electron process. The resulting products of the reduction consisted of the corresponding alpha,beta-unsaturated amine and alpha,beta-saturated ketone. The rate determining step was identified to be the cleavage of N-O bond. In the acidic media the actual leaving group is water and in neutral and moderate basic media hydroxyde ion. (C) 2004 Elsevier B.V. All rights reserved.