title: Chemoenzymatic synthesis of carbasugars from iodobenzene.
abstract: The versatile enantiopure cis-dihydrodiol metabolite 1, formed by bacterial metabolism of iodobenzene, has been used for the synthesis of the pyranose carbasugars (pseudosugars) carba-beta-D-altropyranose 2, carba-alpha-L-galactopyranose 3, carba-beta-D-idopyranose 4 and carba-beta-L-glucopyranose 5. Substitution of the iodine atom by a carbomethoxy group, stereoselective catalytic hydrogenation of an alpha,beta-unsaturated ester, and regioselective inversion of one or two allylic chiral centres are the key steps used in the synthesis of carbasugars 2-5. The relative and absolute configurations of compounds 2-5 were established by a combination of stereochemical correlation, X-ray crystallography and 1H-NMR spectroscopy.
authors.affiliation: Centre for Theory and Application of Catalysis, School of Chemistry, The Queen's University of Belfast, Belfast, UKBT9 5AG.
authors.forename: Derek R
authors.initials: DR
authors.lastname: Boyd
authors.forename: Narain D
authors.initials: ND
authors.lastname: Sharma
authors.forename: Nuria M
authors.initials: NM
authors.lastname: Llamas
authors.forename: John F
authors.initials: JF
authors.lastname: Malone
authors.forename: Colin R
authors.initials: CR
authors.lastname: O'Dowd
authors.forename: Christopher C R
authors.initials: CC
authors.lastname: Allen
mesh_terms: D002241:Carbohydrates / Q000096:biosynthesis*; D018360:Crystallography, X-Ray; D007462:Iodobenzenes / Q000737:chemistry*
chemical_list: D002241:Carbohydrates; D007462:Iodobenzenes; C031905:iodobenzene