Modular synthesis of 1-alpha- and 1-beta-(indol-2-yl)-2'-deoxyribose C-nucleosides

Abstract

A simple two-step method for the selective preparation of anomerically pure 1 alpha- and 1 beta-(indol-2-yl)deoxyribose derivatives was developed. The synthesis was based on the Sonogashira reaction of 1 alpha- and 1 beta-ethynyldeoxyribose and 2-haloanilines followed by a Pd-complex catalyzed cyclization to the corresponding indolyldeoxyribosides.

Keywords

• efficient synthesis
• indole derivatives
• aromatic stacking
• DNA
• cyclization