Synthesis of (-)-morphine.
@article{Taber2002SynthesisO, title={Synthesis of (-)-morphine.}, author={Douglass F. Taber and Timothy D. Neubert and Arnold L. Rheingold}, journal={Journal of the American Chemical Society}, year={2002}, volume={124 42}, pages={ 12416-7 } }
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.
120 Citations
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Total synthesis of (-)-morphine.
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An efficient total synthesis of (-)-morphine in 5% overall yield with the longest linear sequence consisting of 17 steps from 2-cyclohexen-1-one with an N-methyl-DNs-amide moiety is developed.
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A detailed exploration of the synthesis of (-)-morphine based on sequential [3,3]-sigmatropic rearrangements is described, which resulted in the stereoselective formation of the two contiguous carbon centers in a single operation.
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Using an intramolecular nitrone cycloaddition and a Heck cyclization as the crucial transformations, a total synthesis of the racemic morphine alkaloid thebainone A was accomplished in 22 steps…
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The pain ends here: A novel synthetic strategy for the construction of (±)-morphine rings B and E was developed, in which SmI2 -promoted reductive coupling/desulfurization and tandem…
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