Concise Synthesis of Nannozinone A: An Unusual Dihydropyrrolopyrazinone Metabolite From Myxobacteria:

Nannozinone A is an unprecedented dihydropyrrolopyrazinone metabolite derived from myxobacterial Nannocystis pusilla strain MNa10913. In this paper, the synthesis of nannozinone A was disclosed for the first time. Nannozinone A was readily obtained in 6 steps and in 36% overall yield from commercially available N-Boc-propinal. Key feature of the synthesis includes intramolecular imine formation and subsequent spontaneous oxidation toward the unique dihydropyrrolopyrazinone skeleton. This concise synthetic route would be helpful to prepare natural dihydropyrrolopyrazinones and their derivatives.