A. L. Miles, Jonathan Mitchell, Lisa Percy, Jonathan M. Singh, Kuldip Uneyama, E. Total Syntheses of Conformationally Locked Difluorinated Pentopyranose Analogues and a Pentopyranosyl Phosphate Mimetic 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. 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 2007-03-02
    https://acs.figshare.com/articles/dataset/Total_Syntheses_of_Conformationally_Locked_Difluorinated_Pentopyranose_Analogues_and_a_Pentopyranosyl_Phosphate_Mimetic/3020755
10.1021/jo0620258.s004