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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.

Original publication

DOI

10.1039/c4cc02135e

Type

Journal article

Journal

Chem Commun (Camb)

Publication Date

07/08/2014

Volume

50

Pages

8309 - 8311

Keywords

Alkylation, Cyclization, Quinolizidines, Sparteine, Stereoisomerism