Synthesis of Peramine, an Anti-insect Defensive Alkaloid Produced by Endophytic Fungi of Cool Season Grasses

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...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Journal of natural products (Washington, D.C.) D.C.), 2016-04, Vol.79 (4), p.1189-1192
Hauptverfasser:	Nelli, Matthew R, Scheerer, Jonathan R
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkaloids - chemistry Alkaloids - isolation & purification Alkaloids - pharmacology Animals Heterocyclic Compounds, 2-Ring - chemical synthesis Heterocyclic Compounds, 2-Ring - chemistry Heterocyclic Compounds, 2-Ring - pharmacology Molecular Structure Nuclear Magnetic Resonance, Biomolecular Poaceae - chemistry Polyamines - chemical synthesis Polyamines - chemistry Polyamines - pharmacology Seasons
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Beschreibung
Zusammenfassung:	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.
ISSN:	0163-3864 1520-6025
DOI:	10.1021/acs.jnatprod.5b01089