Synthesis of (-)-morphine

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Abstract

The preparation of the diastereomerically pure β-tetralone ketal 4 is reported. Intramolecular alkylidene C-H insertion followed by hydrolysis of 4 proceeded to give the enantiomerically pure cyclopentene 15. The key step in this synthesis was the bis-intramolecular cyclization of keto aldehyde 2 to give the tetracyclic intermediate 20. Enone 20 was converted over several steps to (-)-morphine 1. Copyright © 2002 American Chemical Society.

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Taber, D. F., Neubert, T. D., & Rheingold, A. L. (2002). Synthesis of (-)-morphine. Journal of the American Chemical Society, 124(42), 12416–12417. https://doi.org/10.1021/ja027882h

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