Synthesis of (1′RS,3′SR)- and (1′RS,3′RS)-5-ethyl-5-(3′-hydroxy-1′-methylbutyl)barbituric acid

Abstract

The synthesis of (3RS,5SR)-cis- and (3RS,5RS)-trans-3,5-dimethylvalerolactone and their conversion into (1′RS,3′SR)- and (1′RS,3′RS)-5-ethyl-5-(3′-hydroxy-1′-methylbutyl)barbituric acids, important biotrans-formation products of 5-ethyl-5-(2′-pentyl)barbituric acid (I), is reported, thus establishing the correct structural assignment of these hydroxylated metabolites of (I).