Total syntheses of conformationally-locked difluorinated pentopyranose analogues and a pentopyranosyl phosphate mimetic

Jonathan A. L. Miles, Lisa Mitchell, Jonathan M. Percy, Kuldip Singh, E. Uneyama

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29 Citations (Scopus)
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Abstract

Trifluoroethanol has been elaborated, via a telescoped sequence involving a metalated difluoroenol, a difluoroallylic alcohol, [2,3]-Wittig rearrangement, and ultimately an RCM reaction and requiring minimal intermediate purification, to a number of cyclooctenone intermediates. Epoxidation of these intermediates followed by transannular ring opening or dihydroxylation, then transannular hemiacetalization delivers novel bicyclic analogues of pentopyranoses, which were elaborated (in one case) to an analogue of a glycosyl phosphate.
Original languageEnglish
Pages (from-to)1575-1587
Number of pages13
JournalJournal of Organic Chemistry
Volume72
Issue number5
DOIs
Publication statusPublished - 1 Feb 2007

Keywords

  • chemistry
  • conformationally-locked
  • difluorinated pentopyranose analogues
  • pentopyranosyl phosphate mimetic

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