Towards conformationally-locked difluorosugar analogues: an unexpected sense of dihydroxylation.
Difluorinated cyclooctenones, synthesised using RCM, can be used as templates for stereoselective oxidative transformations to products that undergo transannular reactions to afford conformationally-locked analogues of 2-deoxy-2,2-difluorosugars with different stereochemical relationships between the C-2 and C-3 hydroxyl groups.
Fawcett
John
J
Department of Chemistry, University of Leicester, University Road, Leicester LE1 7RH, UK.
Griffiths
Gerry A
GA
Percy
Jonathan M
JM
Pintat
Stéphane
S
Smith
Clive A
CA
Spencer
Neil S
NS
Uneyama
Emi
E
D002236:Carbohydrate Conformation; D003500:Cyclization; D003837:Deoxy Sugars / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry*; D006900:Hydroxylation; D013237:Stereoisomerism
D003837:Deoxy Sugars; D005461:Fluorine