Fluorinated analogues of amicetose and rhodinose - novel racemic and asymmetric routes

J.M. Percy, R. Roig, K. Singh

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)1058-1071
Number of pages13
JournalEuropean Journal of Organic Chemistry
Issue number7
DOIs
Publication statusPublished - Mar 2009

Keywords

  • synthetic methods
  • carbohydrates
  • fluorination
  • diastereoselectivity
  • epoxidation

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