NOVEL EFFICIENT SYNTHESIS OF 1-ETHOXYVINYL ESTERS USING RUTHENIUM CATALYSTS AND THEIR USE IN ACYLATION OF AMINES AND ALCOHOLS - SYNTHESIS OF HYDROPHILIC 3'-N-ACYLATED OXAUNOMYCIN DERIVATIVES

A novel and efficient synthesis of 1-ethoxyvinyl esters 3a-i from carboxylic acids 4a-i and ethoxyacetylene 5 by using a catalytic amount of ruthenium complex [{RuCl2(p-cymene)}2] 6f has been developed. These reagents reacted smoothly with amines and alcohols to give the corresponding N- and 0-acylated compounds in excellent yields. This acylation method has been applied to the synthesis of hydrophilic 3'-N-acylated oxaunomycin derivatives 13a, b.