Shoko Yamaguchi

Facile syntheses of pseudo-α-d-arabinofuranose, and two pseudo-d-arabinofuranosylnucleosides, (+)-cyclaradine and (+)-1-pseudo-β-d-arabinofuranosyluracil, from d-arabinose

Abstract An optically active pseudo-sugar, pseudo-α- d -arabinofuranose, was efficiently synthesized from d -arabinose by using a stereoselective nitromethane addition reaction to form a branched nitropyranose (6) as a key step. Furthermore, two biologically active pseudo-β- d -arabinofuranosylnucleosides, (+)-cyclaradine and (+)-1-pseudo-β- d -arabinofuranosyluracil, were also synthesized from the nitrocyclopentene derivative (12), which was prepared from a synthetic intermediate of pseudo-arabinofuranose, via Michael-type reaction introducing nucleic acid base moieties.