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

[thumbnail of 329602.pdf]
Preview
Text (329602.pdf)
329602.pdf
Final Published Version

Download (300kB)| Preview

    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

    Miles, Jonathan A. L., Mitchell, Lisa, Percy, Jonathan M. ORCID logoORCID: https://orcid.org/0000-0001-8636-2704, Singh, Kuldip and Uneyama, E.;