title: Catalytic asymmetric total synthesis of (-)-galanthamine and (-)-lycoramine.
abstract: The catalytic asymmetric total syntheses of (-)-galanthamine (1) and (-)-lycoramine (2) have been achieved by using a conceptually new strategy featuring two metal-catalyzed reactions as the key steps. A new method for the construction of 3,4-fused benzofurans has been developed through a palladium-catalyzed intramolecular Larock annulation reaction, which was successfully applied to the construction of the ABD tricyclic skeleton of 1 and 2. To achieve the asymmetric synthesis of 1 and 2, a Sc(III)/N,N'-dioxide complex was used to catalyze the enantioselective conjugate addition of 3-alkyl-substituted benzofuranone to methyl vinyl ketone for the construction of a chiral quaternary carbon center.
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191 (China).
authors.forename: Lei
authors.initials: L
authors.lastname: Li
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191 (China).
authors.forename: Qiao
authors.initials: Q
authors.lastname: Yang
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191 (China).
authors.forename: Yuan
authors.initials: Y
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191 (China). yxjia@bjmu.edu.cn.
authors.forename: Yanxing
authors.initials: Y
authors.lastname: Jia
mesh_terms: D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001572:Benzofurans / Q000138:chemical synthesis / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D005702:Galantamine / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D047151:Amaryllidaceae Alkaloids; D001572:Benzofurans; D001688:Biological Products; D005702:Galantamine; D010165:Palladium; C500482:lycoramine
keywords: alkaloids; asymmetric catalysis; natural products; palladium; total synthesis