During a synthesis of a potential anticancer agent,

Chapter 19, Problem 19.89

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During a synthesis of a potential anticancer agent, 7-hydroxynitidine, the investigators treated bromide 1 with two equivalents of a strong base to form compound 2 (Org. Lett. 1999, 1, 985 988). Propose a plausible mechanism to account for the following ringforming transformation: Br R R OCH2Ph N H O O R R OCH2Ph N H O O 1 2 R = OMe 1) NaNH2 (2 equivalents) 2) H2O

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