title: Enantioselective access to isoquinuclidines by tropenone desymmetrization and homoallylic radical rearrangement: synthesis of (+)-ibogamine.
abstract: [reaction: see text]. Chiral lithium amide-induced desymmetrization of a tropenone and subsequent Bu3SnH-catalyzed nitrogen-directed homoallylic radical rearrangement constitute key steps in a new strategy to dehydroisoquinuclidines. The strategy was applied in a synthesis of (+)-ibogamine.
authors.affiliation: Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK. david.hodgson@chem.ox.ac.uk
authors.forename: David M
authors.initials: DM
authors.lastname: Hodgson
authors.forename: Jean-Marie
authors.initials: JM
authors.lastname: Galano
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D011812:Quinuclidines / Q000737:chemistry*; D013237:Stereoisomerism; D030014:Tabernaemontana / Q000737:chemistry
chemical_list: D000470:Alkaloids; D001952:Bridged-Ring Compounds; D011812:Quinuclidines; C413805:ibogamine