Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 16, Pages 5721-5724Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo100714y
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- Programme Franco-Algerien de Formation Superieure en France (PROFAS)
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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 Cl-substituted alkaloids precursors 9a-c. The syntheses of (+/-)-carnegine, (+/-)-norlaudanosine, and (+/-)-O,O-dimethylcoclaurine have been achieved.
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