title: A General Approach to the Aza-Diketomorpholine Scaffold.
abstract: A stereoconservative three-step synthesis to access to 1,2,4-oxadiazine-3,6-dione is presented. This underexplored platform could be considered as a constrained oxy-azapeptide or an aza-diketomorpholine, the methodology being then successfully applied to produce enantiopure aza-analogs of diketomorpholine natural products. Importantly, the first crystal structures were obtained and compared to diketomorpholine and diketopiperazine structures. Finally, a straightforward procedure concerning the coupling of this heterocyclic scaffold with various amino acids to afford original pseudodipeptide analogs was described.
authors.affiliation: Institut des Biomolécules Max Mousseron, IBMM UMR-5247 CNRS, Université de Montpellier, ENSCM , CC 17-03, Pl. E. Bataillon, 34095 Montpellier Cedex 5, France.
authors.forename: Mathéo
authors.initials: M
authors.lastname: Berthet
authors.affiliation: Institut des Biomolécules Max Mousseron, IBMM UMR-5247 CNRS, Université de Montpellier, ENSCM , CC 17-03, Pl. E. Bataillon, 34095 Montpellier Cedex 5, France.
authors.forename: Baptiste
authors.initials: B
authors.lastname: Legrand
authors.affiliation: Institut des Biomolécules Max Mousseron, IBMM UMR-5247 CNRS, Université de Montpellier, ENSCM , CC 17-03, Pl. E. Bataillon, 34095 Montpellier Cedex 5, France.
authors.forename: Jean
authors.identifier: 0000-0002-4551-4254
authors.initials: J
authors.lastname: Martinez
authors.affiliation: Institut des Biomolécules Max Mousseron, IBMM UMR-5247 CNRS, Université de Montpellier, ENSCM , CC 17-03, Pl. E. Bataillon, 34095 Montpellier Cedex 5, France.
authors.forename: Isabelle
authors.initials: I
authors.lastname: Parrot