Preparation of Carbocyclic C‐Nucleosides from α‐Chlorooxime Precursor

Abstract The syntheses of L ‐carbocyclic benzothiazolo, benzoxazolo, and benzimidazolo C ‐ nor ‐nucleosides are described. The key step is the reaction of the C ‐chlorooxime 7 , obtained by C ‐chlorination with N ‐chlorosuccinimide of [(1 S ,2 R ,3 R ,4 R )‐1‐ tert ‐butyldimethylsiloxy‐2,3‐( O ‐isopropylidenedioxy)]cyclopentane‐4‐carbohydroximic acid ( 6 ), with different α‐amino aromatic compounds. Acidic deprotection gave the benzoxazolo ( 11 ), benzimidazolo ( 12 ), and benzothiazolo ( 13 ) title compounds, in good yields.