Synthesis of bicyclo[3.1.0]hexane derivatives as conformationally restricted analogues of beta-arabinofuranosyl and alpha-galactofuranosyl rings.
A route for the synthesis of bicyclo[3.1.0]hexane-derived conformationally restricted analogues of beta-arabinofuranosyl and alpha-galactofuranosyl rings is described. Advantage is taken of the pseudo-enantiomeric relationship between the two ring systems to develop a route that provides both targets from a single precursor. Key steps include a base-promoted ring contraction of an epoxy ketone obtained from cyclohexane-1,4-dione to give the bicyclo[3.1.0]hexane ring system and a late stage resolution involving esterification with O-acetyl-(S)-mandelic acid.
Li
Jing
J
Alberta Ingenuity Centre for Carbohydrate Science and Department of Chemistry, Gunning-Lemieux Chemistry Centre, University of Alberta, Edmonton, AB T6G 2G2, Canada.
Lowary
Todd L
TL
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D005697:Galactosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001643:Bridged Bicyclo Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D005697:Galactosides; D009005:Monosaccharides; C046059:bicyclo(3.1.0)hexane