title: An efficient asymmetric synthesis of (-)-lupinine.
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.
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK. steve.davies@chem.ox.ac.uk.
authors.forename: Stephen G
authors.initials: SG
authors.lastname: Davies
authors.forename: Ai M
authors.initials: AM
authors.lastname: Fletcher
authors.forename: Emma M
authors.initials: EM
authors.lastname: Foster
authors.forename: Ian T T
authors.initials: IT
authors.lastname: Houlsby
authors.forename: Paul M
authors.initials: PM
authors.lastname: Roberts
authors.forename: Thomas M
authors.initials: TM
authors.lastname: Schofield
authors.forename: James E
authors.initials: JE
authors.lastname: Thomson
mesh_terms: D000478:Alkylation; D003500:Cyclization; D054837:Quinolizidines / Q000737:chemistry; D013034:Sparteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D000093843:Quinolizidine Alkaloids
chemical_list: D054837:Quinolizidines; D013034:Sparteine; C015971:lupinine; D000093843:Quinolizidine Alkaloids