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An efficient asymmetric synthesis of (-)-lupinine.

Authors :
Davies SG
Fletcher AM
Foster EM
Houlsby IT
Roberts PM
Schofield TM
Thomson JE
Source :
Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2014 Aug 07; Vol. 50 (61), pp. 8309-11.
Publication Year :
2014

Abstract

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.

Details

Language :
English
ISSN :
1364-548X
Volume :
50
Issue :
61
Database :
MEDLINE
Journal :
Chemical communications (Cambridge, England)
Publication Type :
Academic Journal
Accession number :
24938152
Full Text :
https://doi.org/10.1039/c4cc02135e