title: Total synthesis of (-)-galanthamine and (-)-lycoramine via catalytic asymmetric hydrogenation and intramolecular reductive Heck cyclization.
abstract: A synthetic strategy featuring efficient ruthenium-catalyzed asymmetric hydrogenation of racemic α-aryloxy cyclic ketone via dynamic kinetic resolution and palladium-catalyzed intramolecular reductive Heck cyclization has been developed for the asymmetric total synthesis of (-)-galanthamine (20.1%, 12 steps) and (-)-lycoramine (40.2%, 10 steps).
authors.affiliation: State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China.
authors.forename: Ji-Qiang
authors.initials: JQ
authors.lastname: Chen
authors.forename: Jian-Hua
authors.initials: JH
authors.lastname: Xie
authors.forename: Deng-Hui
authors.initials: DH
authors.lastname: Bao
authors.forename: Sheng
authors.initials: S
authors.lastname: Liu
authors.forename: Qi-Lin
authors.initials: QL
authors.lastname: Zhou
mesh_terms: D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D005702:Galantamine / Q000138:chemical synthesis* / Q000737:chemistry; D006865:Hydrogenation; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D047151:Amaryllidaceae Alkaloids; D005702:Galantamine; D010165:Palladium; D012428:Ruthenium; C500482:lycoramine