Stereoselective Electrochemical Reduction of 8-Methylene-Oleandomycin

Abstract

The electrochemical reduction of 8-methylene-oleandomycin was investigated by cyclic voltammetry and preparative scale electrolysis. The electrochemical reduction in the exocyclic double bond predominantly gives one epimer with the estimated diastereomeric ratio of 5:1. ͑8S͒-methyl-oleandomycin was identified as the main product of the reaction. Stereoselectivity of the electroreduction was explained by the "bottom-side" adsorption of the 8-methylene-oleandomycin through its conjugated double bond to the electrode surface.