title: A chemoenzymatic total synthesis of (+)-clividine.
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.
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra ACT 0200, Australia.
authors.forename: Lorenzo V
authors.initials: LV
authors.lastname: White
authors.forename: Brett D
authors.initials: BD
authors.lastname: Schwartz
authors.forename: Martin G
authors.initials: MG
authors.lastname: Banwell
authors.forename: Anthony C
authors.initials: AC
authors.lastname: Willis
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D047151:Amaryllidaceae Alkaloids; C569119:clividine; C023825:lycorenine