title: Construction of the tricyclic A-B-C core of the Veratrum alkaloids.
abstract: Organocatalyzed enantioselective allylation of 2-iodocyclohexenone followed by methylation and oxy-Cope rearrangement delivered enantiomerically enriched 2-methyl 3-allyl cyclohexanone, which engaged in acid-catalyzed Robinson annulation to give the bicyclic enone. Subsequent elaboration of the pendant allyl group into an α-diazo β-keto ester set the stage for Rh-mediated cyclization to deliver the tricyclic A-B-C core of the Veratrum alkaloids.
authors.affiliation: Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA. taberdf@udel.edu
authors.forename: Douglass F
authors.initials: DF
authors.lastname: Taber
authors.forename: James F
authors.initials: JF
authors.lastname: Berry
mesh_terms: D003500:Cyclization; D003512:Cyclohexanones / Q000737:chemistry; D015394:Molecular Structure; D014704:Veratrum Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D003512:Cyclohexanones; D014704:Veratrum Alkaloids