Towards a biomimetic synthesis of barrenazine A

Frédéric Buron (1) , Alain Turck (2) , Nelly Plé (3) , Laurent Bischoff (3) , Francis Marsais (2)

1 ICOA - Institut de Chimie Organique et Analytique
2 IRCOF - Institut de Chimie Organique Fine
3 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

We report herein a concise and biomimetic synthesis of a precursor of barrenazine A, a cytotoxic alkaloid. The C2-symmetry of this molecule suggested the dimerization of an aminoketone, as the precursor of the central core pyrazine. This compound was prepared by assembly of aspartic acid and glycine.

Mots clés: Marine alkaloid; Barrenazine; Amino acid; Pyrazine synthesis

Domaines: Chimie; Chimie organique; Chimie thérapeutique; Radiochimie; Matériaux; Chimie inorganique; Catalyse

Frédéric Buron, Alain Turck, Nelly Plé, Laurent Bischoff, Francis Marsais. Towards a biomimetic synthesis of barrenazine A. Tetrahedron Letters, 2007, 48 (25), pp.4327-4330. ⟨10.1016/j.tetlet.2007.04.108⟩. ⟨hal-02385028⟩