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

Miles, Jonathan A. L. and Mitchell, Lisa and Percy, Jonathan M. and Singh, Kuldip and Uneyama, E. (2007) Total syntheses of conformationally-locked difluorinated pentopyranose analogues and a pentopyranosyl phosphate mimetic. Journal of Organic Chemistry, 72 (5). pp. 1575-1587. ISSN 0022-3263 (https://doi.org/10.1021/jo0620258)

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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.

ORCID iDs

Percy, Jonathan M. ORCID: https://orcid.org/0000-0001-8636-2704

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• Item metadata

  Item type:	Article
  ID code:	10279
  Dates:	Date Event 1 February 2007 Published 30 September 2006 Accepted
  Subjects:	Science > Chemistry
  Department:	Unknown Department Faculty of Science > Pure and Applied Chemistry
  Depositing user:	Strathprints Administrator
  Date deposited:	06 Dec 2011 14:26
  Last modified:	11 Nov 2024 09:01
  URI:	https://strathprints.strath.ac.uk/id/eprint/10279