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. 2002 Oct 23;124(42):12416-7.
doi: 10.1021/ja027882h.

Synthesis of (-)-Morphine

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Synthesis of (-)-Morphine

Douglass F Taber et al. J Am Chem Soc. .

Erratum in

  • J Am Chem Soc 2002 Dec 25;124(51):15399

Abstract

The preparation of the diastereomerically pure beta-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.

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