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Rajendra Prasad Korivi and Chien-Hong Cheng Protecting-Group-Free Total Synthesis of Isoquinoline Alkaloids by Nickel-Catalyzed Annulation of o-Halobenzaldimine with an Alkyne as the Key Step Chemistry - A European Journal 16

Article first published online: 10 NOV 2009 | DOI: 10.1002/chem.200902275

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An efficient four-step total synthesis procedure for isoquinolinone alkaloids was developed (see scheme), which features a regioselective nickel-catalyzed formation of the isoquinolinium salt from the corresponding o-bromobenzaldimine and alkyne, in situ conversion to isoquinolinone, oxidation of the primary alcohol functional group followed by an acid-catalyzed intramolecular ring-closing reaction.

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