Tetrahedron
Tetrahedron
5 years ago

New regiocontrolled syntheses of pyrrolopyrazinones and its application to the synthesis of peramine

New regiocontrolled syntheses of pyrrolopyrazinones and its application to the synthesis of peramine
Two novel regiocontrolled syntheses of pyrrolopyrazinones were developed. N-Methylpyrrole amide and 1-bromo-1-alkyne were annulated in the presence of a copper catalyst to give 3-substituted pyrrolopyrazinone in a regioselective manner. In contrast, heating N-methylpyrrole amide with the same haloalkyne in the presence of K3PO4 provided the haloaminal, which was transformed regioselectively into 4-substituted pyrrolopyrazinone. The former procedure was successfully applied to the synthesis of peramine, a natural product isolated from an endophytic fungus.

Publisher URL: www.sciencedirect.com/science

DOI: S0040402017304702

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