title: Stereoselective synthesis and relative configuration assignment of gabosine J.
abstract: The first total synthesis of (+)-gabosine J and that of the epimer at C4 of its enantiomer have been accomplished through an enantioselective approach from a common intermediate 1. These syntheses have allowed us to establish the correct relative configuration of the natural metabolite, which was originally misassigned. This work, together with our former syntheses of other gabosines and related compounds, validates enone 1 as a general synthetic precursor for this kind of carbasugars.
authors.affiliation: Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain.
authors.forename: Miguel Ángel
authors.initials: MÁ
authors.lastname: Fresneda
authors.forename: Ramon
authors.initials: R
authors.lastname: Alibés
authors.forename: Josep
authors.initials: J
authors.lastname: Font
authors.forename: Pau
authors.initials: P
authors.lastname: Bayón
authors.forename: Marta
authors.initials: M
authors.lastname: Figueredo
mesh_terms: D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D003512:Cyclohexanones; C574885:gabosine J