title: Total synthesis of the Amaryllidaceae alkaloid clivonine.
abstract: Two syntheses of the Amaryllidaceae alkaloid clivonine (1) are described. Both employ previously reported 7-arylhydrindane 6 as an intermediate but differ in the method employed for subsequent introduction of what becomes the ring-B lactone carbonyl carbon (C7). The synthesis featuring a Bischler-Napieralski reaction for this transformation constitutes the first asymmetric synthesis of natural (+)-clivonine. Crystal structures for compounds (±)-13, (±)-16, (-)-20 and (±)-28 are also reported.
authors.affiliation: Bayer Schering Pharma AG, Müllerstr. 178, 13353, Berlin, Germany.
authors.forename: Helmut
authors.initials: H
authors.lastname: Haning
authors.forename: Carles
authors.initials: C
authors.lastname: Giró-Mañas
authors.forename: Victoria L
authors.initials: VL
authors.lastname: Paddock
authors.forename: Christian G
authors.initials: CG
authors.lastname: Bochet
authors.forename: Andrew J P
authors.initials: AJ
authors.lastname: White
authors.forename: Gerald
authors.initials: G
authors.lastname: Bernardinelli
authors.forename: Inderjit
authors.initials: I
authors.lastname: Mann
authors.forename: Wolfang
authors.initials: W
authors.lastname: Oppolzer
authors.forename: Alan C
authors.initials: AC
authors.lastname: Spivey
mesh_terms: D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis*; D019684:Magnoliopsida / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: D047151:Amaryllidaceae Alkaloids; C550290:clivonine