AN APPROACH TO THE SYNTHESIS OF PEDERIN

Abstract — Pederin, the vesicant component found in the haemolymph of many species of the staphylinid beetle of the genus Paederus, is a powerful inhibitor of protein synthesis in eucaryotic cells. With its nine chiral centers and its unusual functIonality, it is also the most complex, non—proteinaceous insect defensive compound known. This paper describes our progress toward a total synthesis of this fascinating natural product. Nature's use of organic chemicals for defensive purposes is one of the most intriguing areas of "applied organic chemistry". Arthropods are particularly skillful chemists (1); their defensive agents range from the elegant simplicity of single carbon compounds such as hydro-gen cyanide and formic acid, through a variety of simple aliphatic compounds, to quinones, terpenes and "alkaloids ' (2). Probably the most complex, non—proteinaceous defensive com-pound so far characterized is produced by staphylinid beetles of the genus Paederus (known in East Africa as the "Nairobi Eye Fly'). The dramatic vesicant properties of these beetles were first described in 1912 (3), although the isolation of pederin (the haemolymph compo