Draw a stepwise mechanism for the following reactions, two steps in R. B. Woodwards

Chapter 22, Problem 22.91

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Draw a stepwise mechanism for the following reactions, two steps in R. B. Woodwards classic synthesis of reserpine in 1958. Reserpine, which is isolated from the extracts of the Indian snakeroot Rauwolfi a serpentina Benth, has been used to manage mild hypertension associated with anxiety. N H NH2 CH3O O N H N H H OCOCH3 OCH3 OCH3 CH3OOC CH3OOC CH3OOC OCOCH3 CHO CH3O N H H H N O OCH3 OCH3 OCH3 OCH3 reserpine CH3OOC CH3O O H + [1] , benzene [2] NaBH4, CH3OH several steps

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