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