10.1021/jo201005d.s001 Lorenzo V. White Lorenzo V. White Brett D. Schwartz Brett D. Schwartz Martin G. Banwell Martin G. Banwell Anthony C. Willis Anthony C. Willis A Chemoenzymatic Total Synthesis of (+)-Clividine American Chemical Society 2011 ci alkaloid ee clividine enantiomerically C 11b ent enantiomeric stereochemistry Synthesi diastereoselective addition ClividineThe material Chemoenzymatic pendant cyclohexene compound synthesis 2011-08-05 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/A_Chemoenzymatic_Total_Synthesis_of_Clividine/2625578 The title compound, <i>ent</i>-<b>1</b>, the non-natural enantiomeric form of the lycorenine-type alkaloid (−)-clividine (<b>1</b>), has been prepared using the enantiomerically pure (ee >99.8%) <i>cis</i>-1,2-dihydrocatechol <b>3</b> 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 <i>ent</i>-<b>1</b>.