Synthesis of (-)-morphine

…, TD Neubert, AL Rheingold

Index: Taber, Douglass F.; Neubert, Timothy D.; Rheingold, Arnold L. Journal of the American Chemical Society, 2002 , vol. 124, # 42 p. 12416 - 12417

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Citation Number: 81

Abstract

The preparation of the diastereomerically pure β-tetralone ketal 4 is reported. Intramolecular alkylidene CH 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.

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