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 language | English |
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Pages (from-to) | 1575-1587 |
Number of pages | 13 |
Journal | Journal of Organic Chemistry |
Volume | 72 |
Issue number | 5 |
DOIs | |
Publication status | Published - 1 Feb 2007 |
Keywords
- chemistry
- conformationally-locked
- difluorinated pentopyranose analogues
- pentopyranosyl phosphate mimetic