Tetrahedron Letters p. 1657 - 1660 (1998)
Update date:2022-07-29
Topics:
Siddiqui, Maqbool A.
Driscoll, John S.
Marquez, Victor E.
A convenient route to the anti-HIV active compound, 9-(2,3-dideoxy-2- fluoro-β-D-threo-pentofuranosyl)adenine (1, β-FddA) started with the facile introduction of fluorine at C2' from the α-side of protected 9-(β-D- arabinofuranosyl)adenine (ara-A). Inversion of the stereochemistry at C2' was accomplished via a stable vinyl intermediate (6), which underwent stereoselective reduction of the double bond to give the desired 2'-F-threo isomer with the opposite β-fluoro stereochemistry.
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