Tetrahedron letters

A diastereoselective synthesis of (S, S)-α-fluoro-2, 2-dimethyl-1, 3-dioxolane-4-propanoic acid methyl ester, a key intermediate for the preparation of anti-HIV effective …

MA Siddiqui, VE Marquez, JS Driscoll, JJ Barchi

Index: Siddiqui, Maqbool A.; Marquez, Victor E.; Driscoll, John S.; Barchi, Joseph J. Jr. Tetrahedron Letters, 1994 , vol. 35, # 20 p. 3263 - 3266

Full Text: HTML

Citation Number: 43

Abstract

Abstract (S, S)-α-fluoro-2, 2-dimethyl-1, 3-dioxolane-4-propanoic acid methyl ester (10), a key intermediate for the preparation of anti-HIV active 9-(2, 3-dideoxy-2-fluoro-β-D-threo- pentofuranosyl) adenine (1, FddA) and 1-(2, 3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl) cytosine (2, FddC) was prepared via the diastereoselective fluorination of the chiral imide enolate obtained from 8 with N-fluorobenzenesulfonimide. The overall yield of 10 from the ...