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A chemoenzymatic total synthesis of (+)-Clividine

White, Lorenzo; Schwartz, Brett; Banwell, Martin; Willis, Anthony


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.

CollectionsANU Research Publications
Date published: 2011
Type: Journal article
Source: Journal of Organic Chemistry
DOI: 10.1021/jo201005d


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