Synthesis of tetrahydroisoquinoline alkaloids via anodic cyanation as the key step.
We report a new route to tetrahydroisoquinoline (THIQ) alkaloids involving the alkylation of alpha-aminonitrile 2 as a key step. The latter compound was prepared by anodic cyanation of the corresponding tertiary amine 1. Reductive decyanation of alpha-aminonitriles 6a-c proceeded diastereoselectively (up to 95% de) to deliver the C1-substituted alkaloids precursors 9a-c. The syntheses of (+/-)-carnegine, (+/-)-norlaudanosine, and (+/-)-O,O-dimethylcoclaurine have been achieved.
Louafi
Fadila
F
Département de Chimie, Faculté des Sciences Exactes,Université Mentouri de Constantine, Route de Ain El Bey,25000 Constantine, Algérie.
Hurvois
Jean-Pierre
JP
Chibani
Aïssa
A
Roisnel
Thierry
T
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis* / Q000737:chemistry
D000470:Alkaloids; D009570:Nitriles; D044005:Tetrahydroisoquinolines