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 ring- forming transformation. For the mechanism, draw the curved arrows as needed. Include lone pairs and charges in your answer. Do not draw out any hydrogen explicitly in your products. Do not use abbreviations such as Me or Ph. Br R 1) NaNH2 (2 equivalents) 2) H2O 0 H OCH,Ph 1 R = OMe R N. R OCH Ph 2