A General Approach to the Aza-Diketomorpholine Scaffold
Mathéo Berthet1, Baptiste Legrand1, Jean Martinez1
1Institut des Biomolécules Max Mousseron, IBMM UMR-5247 CNRS, Université de Montpellier, ENSCM , CC 17-03, Pl. E. Bataillon, 34095 Montpellier Cedex 5, France.
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.
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