title: Synthesis of 4-membered carbasugars by way of stereoselective SmI2-mediated aldehyde-alkene cyclization.
abstract: A stereodivergent synthesis of the first examples of 4-membered carbasugars has been achieved from vitamin C by way of an efficient intramolecular SmI2-mediated aldehyde-alkene coupling. In this key step, cylobutanes with four contiguous asymmetric centers are generated with a high level of stereocontrol.
authors.affiliation: Laboratoire de Synthèse Organique et Molécules Bioactives, Université de Strasbourg/CNRS (UMR 7509), Ecole Européenne de Chimie, Polymères et Matériaux, 25 rue Becquerel, 67087 Strasbourg, France.
authors.forename: Pierre-Antoine
authors.initials: PA
authors.lastname: Nocquet
authors.forename: Damien
authors.initials: D
authors.lastname: Hazelard
authors.forename: Guillaume
authors.initials: G
authors.lastname: Gruntz
authors.forename: Philippe
authors.initials: P
authors.lastname: Compain
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D054329:Carbasugars / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000475:Alkenes; D054329:Carbasugars