title: A new entry to Amaryllidaceae alkaloids from carbohydrates: total synthesis of (+)-vittatine.
abstract: The stereoselective and chiral synthesis of the Amaryllidaceae alkaloid, (+)-vittatine 1, is described; the quaternary carbon in 1 was generated by Claisen rearrangement of a cyclohexenol derived from D-glucose by way of a Ferrier's carbocyclisation reaction and a hexahydroindole skeleton was effectively constructed by intramolecular aminomercuration-demercuration, followed by Chugaev reaction.
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Masahiro
authors.initials: M
authors.lastname: Bohno
authors.forename: Hidetomo
authors.initials: H
authors.lastname: Imase
authors.forename: Noritaka
authors.initials: N
authors.lastname: Chida
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D002241:Carbohydrates; D010617:Phenanthridines; C488939:vittatine 1