Abstract
The unexpected domino coupling and rearrangement of the Cinchona alkaloid skeleton has been found to occur in the reaction of 9-chloro-9-deoxy-alkaloids with Grignards from peri-dihalogenonaphthalene. The cyclization and migration of the central quinuclidinylmethyl group (C9) from position C-4′ to position C-3′ of quinoline formed a novel chiral ring system of 5-aza-7H-benzo[no]tetraphene, yielding products of unlike configuration. The proposed reaction pathway involves radical intermediates.
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