title: Total synthesis of (-)-normalindine via addition of metalated 4-methyl-3-cyanopyridine to an enantiopure sulfinimine.
abstract: A concise total asymmetric synthesis of the tetrahydronaphthyridine alkaloid (-)-normalindine has been accomplished via the addition of a laterally metalated 4-methyl-3-cyanopyridine to a sulfinimine (N-sulfinyl imine) as the key step.
authors.affiliation: Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@temple.edu
authors.forename: Franklin A
authors.initials: FA
authors.lastname: Davis
authors.forename: Jeffrey Y
authors.initials: JY
authors.lastname: Melamed
authors.forename: Steven S
authors.initials: SS
authors.lastname: Sharik
mesh_terms: D007097:Imines / Q000737:chemistry*; D008968:Molecular Conformation; D009287:Naphthyridines / Q000138:chemical synthesis* / Q000737:chemistry; D009570:Nitriles / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry*
chemical_list: C522014:4-methyl-3-cyanopyridine; D007097:Imines; D009287:Naphthyridines; D009570:Nitriles; D011725:Pyridines; D013452:Sulfonium Compounds; C522015:normalindine; C522016:sulfinimine