Towards a biomimetic synthesis of barrenazine A

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.

An analogue of barrenazine A was prepared in eight steps with a 29% overall yield, from protected aspartic acid.