title: Synthesis of Peramine, an Anti-insect Defensive Alkaloid Produced by Endophytic Fungi of Cool Season Grasses.
abstract: A seven-step synthesis of peramine, which required three chromatographic separations, is described. Key to the synthesis is an enolate alkylation of a pyrrole-fused diketopiperazine, reduction of the acyl pyrrole, and dehydration of the intermediate pyrrolyl carbinol to establish the pyrrolopyrazine core of peramine.
authors.affiliation: Department of Chemistry, The College of William & Mary , P.O. Box 8795, Williamsburg, Virginia 23187, United States.
authors.forename: Matthew R
authors.initials: MR
authors.lastname: Nelli
authors.affiliation: Department of Chemistry, The College of William & Mary , P.O. Box 8795, Williamsburg, Virginia 23187, United States.
authors.forename: Jonathan R
authors.initials: JR
authors.lastname: Scheerer
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D006109:Poaceae / Q000737:chemistry*; D011073:Polyamines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D012621:Seasons
chemical_list: D000470:Alkaloids; D006574:Heterocyclic Compounds, 2-Ring; D011073:Polyamines; C499007:peramine