A Completely Diastereoselective Electrophilic Fluorination of a Chiral, Noncarbohydrate Sugar Ring Precursor: Application to the Synthesis of Several Novel 2'- …
JJ McAtee, RF Schinazi, DC Liotta
Index: Jeffrey McAtee; Schinazi, Raymond F.; Liotta, Dennis C. Journal of Organic Chemistry, 1998 , vol. 63, # 7 p. 2161 - 2167
Full Text: HTML
Citation Number: 74
Abstract
A new and completely diastereoselective method for the introduction of fluorine into a noncarbohydrate sugar ring precursor has been developed. The use of N- fluorodibenzenesulfonimide (5) for the electrophilic fluorination of chiral lactone 4, which is derived from l-glutamic acid, yields the key intermediate 6. This is transformed into an anomeric acetate 8 and is used for the synthesis of a number of novel α-2'- ...
Related Articles:
Chemistry and anti-HIV properties of 2'-fluoro-2', 3'-dideoxyarabinofuranosylpyrimidines
[Siddiqui; Driscoll; Marquez; Roth; Shirasaka; Mitsuya; Barchi Jr.; Kelley Journal of Medicinal Chemistry, 1992 , vol. 35, # 12 p. 2195 - 2201]
The synthesis of novel 3′, 5′-homocyclic nucleotides as potential anti-HIV agents
[Drew, Michael G. B.; Gorsuch, Stephen; Gould, Jayne H. M.; Mann, John Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 8 p. 969 - 978]