Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 15, Pages 6250-6257Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo201005d
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Funding
- Australian Research Council
- Institute of Advanced Studies
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The title compound, ent-1, the non-natural enantiomeric form of the lycorenine-type alkaloid (-)-clividine (1), has been prepared using the enantiomerically pure (ee >99.8%) cis-1,2-dihydrocatechol 3 as starting material. A key feature associated with the closing stages of the synthesis involved the diastereoselective addition of a nitrogen-centered radical onto a pendant cyclohexene to establish the cis-fused D-ring and the required stereochemistry at C11b in the final product ent-1.
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