Synthesis and applications of fluorinated nucleoside analogues

The Orthoester Johnson–Claisen Rearrangement in the Synthesis of Bioactive Molecules, Natural Products, and Synthetic Intermediates – Recent Advances

“…[34] Claisen rearrangement of allyl α-bromo esters in the presence of In/InCl 3 was studied by Ishihara and Hatakeyama. [37] Qing and coworkers [38] designed and synthesized 2Ј,3Ј-dideoxy-6Јfluorocarbocyclic nucleosides starting from allyl alcohol 44 (Scheme 12). A review on the Reformatskii-Claisen rearrangement has recently been compiled.…”

“…[36] Chemically modified nucleosides are interesting targets in view of their high bioactivity profile. [37] Qing and coworkers [38] designed and synthesized 2Ј,3Ј-dideoxy-6Јfluorocarbocyclic nucleosides starting from allyl alcohol 44 (Scheme 12). Esterification of this allyl alcohol with bromofluoroacetyl chloride gave allyl bromofluoroacetate 45.…”

Synthesis of 4-amino-5-fluoropyrimidines and 5-amino-4-fluoropyrazoles from a β-fluoroenolate salt

“…Fluorinated pyrimidines, pyrimidine analogues and pyrazoles [20,21] play a prominent role in several clinically important pharmaceuticals [22][23][24][25]. These compounds act against HIV or HIV-related diseases [26], such as opportunistic fungal infections, and represent nucleoside analogues which can either act as antimetabolites or as nucleoside reverse transcriptase inhibitors (NRTIs).…”

Synthesis and antiviral evaluation of 2′,2′,3′,3′-tetrafluoro nucleoside analogs

“…In the field of nucleoside analogs, 2 introduction of fluorine has proven to be successful and has led to several very widely prescribed drugs such as (−)-FTC (HIV), gemcitabine (cancer), or more recently sofosbuvir (hepatitis C virus, HCV) (Figure 1). In addition to the approved fluorinated nucleosides discussed above, several fluorine-containing analogs have been reported in the literature to have attractive antiviral profiles, although some proved too toxic for human use.…”