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

Percy, J.M. and Mitchell, L. and Singh, K. and Uneyama, E. and Miles, J.A.L. (2007) Total syntheses of conformationally-locked difluorinated pentopyranose analogues and a pentopyranosyl phosphate mimetic. Journal of Organic Chemistry, 72. pp. 1575-1587. ISSN 0022-3263

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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.

Item type: Article
ID code: 10279
Keywords: chemistry, conformationally-locked , difluorinated pentopyranose analogues , pentopyranosyl phosphate mimetic, Chemistry, Organic Chemistry
Subjects: Science > Chemistry
Department: Faculty of Science > Pure and Applied Chemistry
Unknown Department
Depositing user: Strathprints Administrator
Date Deposited: 06 Dec 2011 14:26
Last modified: 21 May 2015 10:35
URI: http://strathprints.strath.ac.uk/id/eprint/10279

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