N. OH (-)-hyoscyamine (-)-littorine

Chemistry for Today: General, Organic, and Biochemistry
9th Edition
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Chapter17: Carbohydrates
Section: Chapter Questions
Problem 17.47E
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(−)-Hyoscyamine, an optically active drug used to treat gastrointestinal disorders, is isolated from Atropa belladonna, the deadly nightshade plant, by a basic aqueous extraction procedure. If too much base is used during isolation, optically inactive material is isolated. (a) Explain this result by drawing a stepwise mechanism. (b) Explain why littorine, an isomer
isolated from the tailower plant in Australia, can be obtained optically pure regardless of the amount of base used during isolation.

N.
OH
(-)-hyoscyamine
(-)-littorine
Transcribed Image Text:N. OH (-)-hyoscyamine (-)-littorine
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