Studies concerning the antibiotic actinonin. Part II. Total synthesis of actinonin and some structural analogues by the isomaleimide method

Abstract

A general method for the synthesis of actinonin (I) and several structural analogues is described. L-Valyl-L-prolinol (III) and the isomaleimide (XIV) yield the intermediate (XVII), which gives actinonin (I) on hydrogenation. Corresponding routes yield compounds (XXV)(L-alanylpyrrolidine and DL-alanylpyrrolidine analogues), (XXVI)(L-valylpyrrolidine analogue), and (XXVII)(L-valyl-L-prolinol analogue), which are actinonin analogues lacking the pentyl side-chain.