DESTRUXIN ANALOGS - VARIATIONS OF THE ALPHA-HYDROXY ACID SIDE-CHAIN

This work describes the synthesis of three destruxin E cyclodepsipepti dic analogs. These compounds have an identical amino acid sequence but differ by the nature of the hydroxy acid residue which is 2-hydroxy-3 -phenylpropionic (Hpp) 2-hydroxy-5-trimethylsilyl-4-pentynoic (Hpy-TMS ) and 3-hydroxy-4-pentynoic (Hpy) acid, respectively. The insecticidal properties on the Galleria mellollella larvae (paralysis and lethal e ffect) of these analogs are presented in comparison with the natural d estruxin E. All these compounds have toxic effects the most potent bei ng Hpy that induces the same effect as destruxin E. (C) Munksgaard 199 7.