Asymmetric synthesis of 2-deoxy-2-fluoro-γ-aldonolactones and their conversion to 2-deoxy-2-fluoropentoses

Article abstract of DOI:10.1016/0040-4039(96)00825-8

2-Fluoro-2-deoxy-γ-xylonic and -lyxonic lactones, 7a and 7b, were prepared via the diastereoselective fluorination of the α,β-unsaturated chiral imide 5 followed by dihydroxylation. Lactones 7a and 7b were converted to 2-deoxy-2-fluoro-xylo-D-pyranose (1) and 2-deoxy-2-fluoro-lyxo-L-pyranose (2) by reduction and deprotection.