Total synthesis of (-)-normalindine via addition of metalated 4-methyl-3-cyanopyridine to an enantiopure sulfinimine.
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.
Davis
Franklin A
FA
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@temple.edu
Melamed
Jeffrey Y
JY
Sharik
Steven S
SS
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*
C522014:4-methyl-3-cyanopyridine; D007097:Imines; D009287:Naphthyridines; D009570:Nitriles; D011725:Pyridines; D013452:Sulfonium Compounds; C522015:normalindine; C522016:sulfinimine