Total Syntheses of Conformationally Locked Difluorinated Pentopyranose Analogues and a Pentopyranosyl Phosphate Mimetic Jonathan A. L. Miles Lisa Mitchell Jonathan M. Percy Kuldip Singh E. Uneyama 10.1021/jo0620258.s004 https://acs.figshare.com/articles/dataset/Total_Syntheses_of_Conformationally_Locked_Difluorinated_Pentopyranose_Analogues_and_a_Pentopyranosyl_Phosphate_Mimetic/3020755 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. 2007-03-02 00:00:00 sequence Total Syntheses novel bicyclic analogues RCM reaction Pentopyranosyl Phosphate MimeticTrifluoroethanol metalated difluoroenol Difluorinated Pentopyranose Analogues pentopyranose Wittig transannular ring opening Epoxidation Conformationally glycosyl phosphate dihydroxylation difluoroallylic alcohol transannular hemiacetalization purification cyclooctenone intermediates rearrangement