Total Synthesis of Peramine

Article abstract of DOI:10.1021/jo00255a002

A facile synthesis of 1-oxo-2,3-disubstituted-pyrrolo<1,2-a>pyrazines, which involves the reaction of 2-(trichloroacetyl)pyrrole (3) with halomethyl ketones (to give pyrrolo<2,1-c><1,4>oxazin-1-ones) followed by successive treatment with methylamine and acid, has been developed.This methodology has been applied to the total synthesis of the insect feeding deterrent peramine (1).