A convergent approach to heterocycle synthesis via silver ion mediated. alpha.-ketoimidoyl halide-arene cyclizations. An application to the synthesis of the erythrinane …

M Westling, R Smith, T Livinghouse

Index: Westling, Mark; Smith, Richard; Livinghouse, Tom Journal of Organic Chemistry, 1986 , vol. 51, # 8 p. 1159 - 1165

Full Text: HTML

Citation Number: 72

Abstract

a-Keto imidoyl halides formed by the reaction of representative 2-phenylethyl and related isocyanides with acyl halides undergo facile cyclization induced by silver salts to provide the corresponding heterocycles in good to excellent yield. An efficient synthesis of the erythrinane skeletal system which relies upon the sequential utilization of this method followed by an azomethine ylide [3+ 21 cycloaddition reaction is described.