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Issue 61, 2014
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An efficient asymmetric synthesis of (−)-lupinine

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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.

Graphical abstract: An efficient asymmetric synthesis of (−)-lupinine

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Publication details

The article was received on 22 Mar 2014, accepted on 08 Jun 2014 and first published on 09 Jun 2014


Article type: Communication
DOI: 10.1039/C4CC02135E
Citation: Chem. Commun., 2014,50, 8309-8311
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    An efficient asymmetric synthesis of (−)-lupinine

    S. G. Davies, A. M. Fletcher, E. M. Foster, I. T. T. Houlsby, P. M. Roberts, T. M. Schofield and J. E. Thomson, Chem. Commun., 2014, 50, 8309
    DOI: 10.1039/C4CC02135E

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