Diastereoselective Synthesis of Allosecurinine and Viroallosecurinine from Menisdaurilide

A new and versatile synthetic route to Securinega alkaloids is reported. The first synthesis of allosecurinine has been accomplished in seven steps and 40% yield, starting from (+)-menisdaurilide, using a vinylogous Mannich reaction as the key transformation. Similarly, viroallosecurinine has been s...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Journal of organic chemistry 2008-10, Vol.73 (19), p.7657-7662
Hauptverfasser:	Bardají, Gisela G, Cantó, Mariona, Alibés, Ramón, Bayón, Pau, Busqué, Félix, de March, Pedro, Figueredo, Marta, Font, Josep
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkaloids - chemical synthesis Azepines - chemical synthesis Benzofurans - chemistry Chemistry Euphorbiaceae Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Heterocyclic Compounds, Bridged-Ring - chemical synthesis Lactones - chemical synthesis Organic chemistry Piperidines - chemical synthesis Preparations and properties Stereoisomerism
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Beschreibung
Zusammenfassung:	A new and versatile synthetic route to Securinega alkaloids is reported. The first synthesis of allosecurinine has been accomplished in seven steps and 40% yield, starting from (+)-menisdaurilide, using a vinylogous Mannich reaction as the key transformation. Similarly, viroallosecurinine has been synthesized from (−)-menisdaurilide.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo801470u