Carbocyclic Sugar Amines: Synthesis and Stereochemistry of Racemic α- and β-Carbocyclic Ribofuranosylamine, Carbocyclic Lyxofuranosylamine, and Related Compounds

Article abstract of DOI:10.1021/jo00329a026

The facile and stereoselective synthesis of racemic carbocyclic β-ribofuranosylamine, carbocyclic β-lyxofuranosylamine, and related 2,3-cis-dihydroxy carbocyclic pentofuranosylamines is reported.In addition, the synthesis, isolation, and base-catalyzed epimerization of methyl cis-4-aminocyclopent-2-enecarboxylate are described.The epimerization at C(1) followed by stereoselective cis hydroxylation provides for the first time access to the racemic carbocyclic α-pentofuranosylamines.