An efficient asymmetric synthesis of (?)-lupinine??

Chemical Communications Pub Date: 2014-06-09 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.

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