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An efficient asymmetric synthesis of (-)-lupinine
Stephen G Davies1, Ai M Fletcher, Emma M Foster
1Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK. steve.davies@chem.ox.ac.uk.
Chemical Communications (Cambridge, England)
|June 19, 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.