Formation of the Pyridazine Natural Product Azamerone by Biosynthetic Rearrangement of an Aryl Diazoketone

Abstract

All in the family: Knowledge of the biosynthesis of NN containing natural products is limited. Feeding experiments with 13C and 15N-labeled molecules establish that the phthalazinone core of azamerone is derived from the diazo chlorinated meroterpenoid SF2415A3. A biosynthetic mechanism involving an oxidative rearrangement of the aryl diazoketone followed by rearomatization with the dinitrogen group is proposed.