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Article Dans Une Revue Journal of Organic Chemistry Année : 2010

Synthesis of tetrahydroisoquinoline alkaloids via anodic cyanation as the key step.

Résumé

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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Dates et versions

hal-00737539 , version 1 (02-10-2012)

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Fadila Louafi, Jean-Pierre Hurvois, Aïssa Chibani, Thierry Roisnel. Synthesis of tetrahydroisoquinoline alkaloids via anodic cyanation as the key step.. Journal of Organic Chemistry, 2010, 75 (16), pp.5721-4. ⟨10.1021/jo100714y⟩. ⟨hal-00737539⟩
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