An efficient asymmetric synthesis of (-)-lupinine

The asymmetric synthesis of (-)-lupinine was achieved in 8 steps, 15% overall yield and >99 : 1 dr from commercially available starting materials. The strategy used for the construction of the quinolizidine scaffold involved reaction of an enantiopure tertiary dibenzylamine via two sequential rin...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Chemical communications (Cambridge, England) England), 2014-08, Vol.50 (61), p.8309-8311
Hauptverfasser:	Davies, Stephen G, Fletcher, Ai M, Foster, Emma M, Houlsby, Ian T T, Roberts, Paul M, Schofield, Thomas M, Thomson, James E
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkylation Asymmetry Cyclization Quinolizidines - chemistry Scaffolds Sparteine - analogs & derivatives Sparteine - chemical synthesis Sparteine - chemistry Stereoisomerism Strategy Synthesis
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Beschreibung
Zusammenfassung:	The asymmetric synthesis of (-)-lupinine was achieved in 8 steps, 15% overall yield and >99 : 1 dr from commercially available starting materials. The strategy used for the construction of the quinolizidine scaffold involved reaction of an enantiopure tertiary dibenzylamine via two sequential ring-closures which both occurred with concomitant N-debenzylation.
ISSN:	1359-7345 1364-548X
DOI:	10.1039/c4cc02135e