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Synthesis of 4-membered carbasugars by way of stereoselective SmI2-mediated aldehyde-alkene cyclization. 2013

Pierre-Antoine Nocquet, and Damien Hazelard, and Guillaume Gruntz, and Philippe Compain
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.

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.

UI MeSH Term Description Entries
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D003500 Cyclization Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Cyclizations
D000447 Aldehydes Organic compounds containing a carbonyl group in the form -CHO. Aldehyde
D000475 Alkenes Unsaturated hydrocarbons of the type Cn-H2n, indicated by the suffix -ene. (Grant & Hackh's Chemical Dictionary, 5th ed, p408) Alkene,Olefin,Olefins,Pentene,Pentenes
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D054329 Carbasugars Sugar analogs in which the ring oxygen is replaced by a methylene (CH2) carbon. Carba-Monosaccharide,Carba-Sugar,Carbasugar,Pseudosugar,Carba-Monosaccharides,Carba-Sugars,Pseudosugars,Carba Monosaccharide,Carba Monosaccharides,Carba Sugar,Carba Sugars

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