title: Enantioselective synthesis and absolute configuration assignment of gabosine O. Synthesis of (+)- and (-)-gabosine N and (+)- and (-)-epigabosines N and O.
abstract: [reaction: see text] A rational approach to the synthesis of gabosines and other related carba-sugars starting from a masked p-benzoquinone has been designed. The enantioselective acetylation of the hydroxyketal 2 provides a practical entry to either enantiomer of the target products. The strategy has been applied to the synthesis of (+)- and (-)-gabosines N and O and (+)- and (-)-epigabosines N and O. The absolute configuration of natural gabosine O has been established.
authors.affiliation: Universitat Autonoma de Barcelona, Departament de Química, 08193 Bellaterra, Spain.
authors.forename: Ramón
authors.initials: R
authors.lastname: Alibés
authors.forename: Pau
authors.initials: P
authors.lastname: Bayón
authors.forename: Pedro
authors.initials: P
authors.lastname: de March
authors.forename: Marta
authors.initials: M
authors.lastname: Figueredo
authors.forename: Josep
authors.initials: J
authors.lastname: Font
authors.forename: Georgina
authors.initials: G
authors.lastname: Marjanet
mesh_terms: D016227:Benzoquinones / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003512:Cyclohexanones; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D016227:Benzoquinones; D003512:Cyclohexanones; C516134:gabosine N