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.

Keywords: Marine alkaloid; Barrenazine; Amino acid; Pyrazine synthesis

Domains: Chemical Sciences; Chemical Sciences; Organic chemistry; Chemical Sciences; Medicinal Chemistry; Chemical Sciences; Radiochemistry; Chemical Sciences; Material chemistry; Chemical Sciences; Inorganic chemistry; Chemical Sciences; Catalysis

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⟩