Facile Synthesis of β- and α‑Arabinofuranosides and Application to Cell Wall Motifs of <i>M. tuberculosis</i>

Abstract

Propargyl 1,2-orthoesters of arabinose are exploited for the synthesis of 1,2-<i>trans</i> furanosides; easily accessible 1,2-trans ribofuranosides are converted to challenging 1,2-<i>cis</i>-arabinofuranosides by oxidoreduction. Utility of these protocols was demonstrated by the successful synthesis of major structural motifs present in the cell surface of <i>Mycobacterium tuberculosis.</i> Key furanosylations were carried out under gold-catalyzed glycosidation conditions