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  • Title: Synthesis of tetrahydroisoquinoline alkaloids via anodic cyanation as the key step.
    Author: Louafi F, Hurvois JP, Chibani A, Roisnel T.
    Journal: J Org Chem; 2010 Aug 20; 75(16):5721-4. PubMed ID: 20704442.
    Abstract:
    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.
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