An unusual occurrence on attempted purine C-8 electrophilic fluorination of 5'-noraristeromycin.
Reaction of the in situ generated purine C-8 carbanion of a protected 5'-noraristeromycin derivative with N-fluorobenzenesulfonimide gave 8-phenylsulfonyl-5'-noraristeromycin rather than the expected 8-fluoro derivative. A single electron transfer (SET) mechanism is proposed for this occurrence. The phenylsulfonyl product offers a structural feature common to some anti-HIV agents. [reaction: see text]
Roy
Atanu
A
Department of Chemistry and Biochemistry, Auburn University, Auburn, AL 36849-5312, USA.
Schneller
Stewart W
SW
D000241:Adenosine / Q000031:analogs & derivatives* / Q000737:chemistry; D019380:Anti-HIV Agents / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D015394:Molecular Structure; D011687:Purines / Q000737:chemistry*
D019380:Anti-HIV Agents; D006845:Hydrocarbons, Fluorinated; D011687:Purines; C076829:5'-noraristeromycin; D000241:Adenosine