title: A potentially divergent and rapid route to analogues of deoxycyclitols, pentopyranoses, 6-deoxyhexoses, and hexoses.
abstract: Direct precursors to analogues of pentopyranoses, 6-deoxyhexoses, and hexoses, in which a CF(2) center replaces the pyranose oxygen, have been synthesized rapidly from trifluoroethanol. A simple scaleable allylation reaction delivers ethers which undergo dehydrofluorination/metalation, followed by addition to either acrolein or cinnamaldehyde, to afford allylic alcohols. Fluorine-assisted [3,3]-rearrangement followed by reduction with sodium borohydride delivers diols, which undergo RCM smoothly to afford cyclohexene diols.
authors.affiliation: Department of Chemistry, University of Leicester, University Road, Leicester LE1 7RH, UK.
authors.forename: Christophe
authors.initials: C
authors.lastname: Audouard
authors.forename: John
authors.initials: J
authors.lastname: Fawcett
authors.forename: Gerry A
authors.initials: GA
authors.lastname: Griffith
authors.forename: Erwan
authors.initials: E
authors.lastname: Kérourédan
authors.forename: Afjal
authors.initials: A
authors.lastname: Miah
authors.forename: Jonathan M
authors.initials: JM
authors.lastname: Percy
authors.forename: Hongli
authors.initials: H
authors.lastname: Yang