title: [Synthesis of potential metabolites of a barbiturate containing two branched side chains].
abstract: The two branched side chains of 5-(3-methylbutyl)-5-(2-methylpropyl)-barbituric acid present a tertiary carbon atom, which can be oxidized in vivo by hepatic enzymes. Potential metabolites of this compound are synthesised: the gamma-hydroxy metabolite can be oxidized directly by CrO3 while the beta-hydroxy metabolite can only be prepared by hydration of a double bond. This beta-hydroxybarbiturate then undergoes an alcoholysis leading to an allophanyl-gamma-lactone, which is hydrolysed into a carboxylic lactone, which can give a lactone by decarboxylation. On the other hand, a beta-gamma-dihydroxymetabolite is synthesised by double hydration of two double bonds using two different methods. A spirobilactone can also be synthesised from this dihydroxy compound.
authors.forename: A
authors.initials: A
authors.lastname: Talab
authors.forename: C
authors.initials: C
authors.lastname: Cavé
authors.forename: S
authors.initials: S
authors.lastname: Ménager
authors.forename: M
authors.initials: M
authors.lastname: Miocque
authors.forename: O
authors.initials: O
authors.lastname: Lafont
mesh_terms: D001463:Barbiturates / Q000138:chemical synthesis*; D008968:Molecular Conformation; D010084:Oxidation-Reduction
chemical_list: D001463:Barbiturates
vernacular_title: Synthèse des métabolites potentiels d'un barbiturique porteur de deux chaînes ramifiées.