An efficient asymmetric synthesis of (-)-lupinine.
Davies SG., Fletcher AM., Foster EM., Houlsby ITT., Roberts PM., Schofield TM., Thomson JE.
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.