2. Academic Validation
  3. An efficient asymmetric synthesis of (-)-lupinine

An efficient asymmetric synthesis of (-)-lupinine

  • Chem Commun (Camb). 2014 Aug 7;50(61):8309-11. doi: 10.1039/c4cc02135e.
Stephen G Davies 1,  Ai M Fletcher,  Emma M Foster,  Ian T T Houlsby,  Paul M Roberts,  Thomas M Schofield,  James E Thomson
Affiliations

Affiliation

  • 1 Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK. [email protected].
PMID: 24938152 DOI: 10.1039/c4cc02135e
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.

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