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

J.M. Percy, L. Mitchell, K. Singh, E. Uneyama, J.A.L. Miles

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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
DOIs
Publication statusPublished - 2007

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Trifluoroethanol
Epoxidation
Purification
Phosphates
Alcohols

Keywords

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

Cite this

Percy, J.M. ; Mitchell, L. ; Singh, K. ; Uneyama, E. ; Miles, J.A.L. / Total syntheses of conformationally-locked difluorinated pentopyranose analogues and a pentopyranosyl phosphate mimetic. In: Journal of Organic Chemistry. 2007 ; Vol. 72. pp. 1575-1587.
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Total syntheses of conformationally-locked difluorinated pentopyranose analogues and a pentopyranosyl phosphate mimetic. / Percy, J.M.; Mitchell, L.; Singh, K.; Uneyama, E.; Miles, J.A.L.

In: Journal of Organic Chemistry, Vol. 72, 2007, p. 1575-1587.

Research output: Contribution to journalArticle

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AU - Percy, J.M.

AU - Mitchell, L.

AU - Singh, K.

AU - Uneyama, E.

AU - Miles, J.A.L.

PY - 2007

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KW - chemistry

KW - conformationally-locked

KW - difluorinated pentopyranose analogues

KW - pentopyranosyl phosphate mimetic

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