Fluorinated analogues of amicetose and rhodinose - novel racemic and asymmetric routes
Percy, J.M. and Roig, R. and Singh, K. (2009) Fluorinated analogues of amicetose and rhodinose - novel racemic and asymmetric routes. European Journal of Organic Chemistry (7). pp. 1058-1071. ISSN 1434-193X (http://dx.doi.org/10.1002/ejoc.200801130)
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Trifluoroethanol was converted into difluorinated (racemic) analogues of amicetose and rhodinose by metallated difluoroenol acetal chemistry, protection, release of the latent difluoromethyl ketone, stereoselective reduction and ozonolysis in acidic methanol. A fortuitous separation of diastereoisomers allowed the diastereoisomeric pyranoses to be obtained cleanly. Though reductive defluorination allowed a facile entry to the route, the corresponding monofluoro sugar analogues could not be separated. Instead, Sharpless asymmetric epoxidation followed by epoxide ring-opening with an unusual nucleophilic fluoride source allowed enantiomerically highly enriched and selectively protected fluorodiols to be obtained. Ozonolysis then afforded the methyl pyranosides, which could be transformed in a number of ways.
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Item type: Article ID code: 19246 Dates: DateEventMarch 2009PublishedSubjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry Depositing user: Strathprints Administrator Date deposited: 14 Jun 2010 13:32 Last modified: 08 Apr 2024 17:49 URI: https://strathprints.strath.ac.uk/id/eprint/19246