Abstract
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.
Original language | English |
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Pages (from-to) | 6250-6257 |
Number of pages | 8 |
Journal | Journal of Organic Chemistry |
Volume | 76 |
Issue number | 15 |
DOIs | |
Publication status | Published - 5 Aug 2011 |