CAN-Mediated Synthesis of 2-Deoxy Sugars: Access to Chiral 2-Deoxy 3-Bisindolyl-<i>C</i>-glycosides

The 2-deoxy sugars and bisindole moieties are ubiquitously found in natural products and play a crucial role in medicinal chemistry and chemical biology. Herein, we report a novel, quick, and highly effective technique that utilizes ceric ammonium nitrate (CAN) to synthesize 2-deoxy sugars from various protected glycals within 1-2 h. Additionally, we further explore the new process of transforming 2-deoxy sugars into chirally pure 2-deoxy-3-bisindolyl-<i>C</i>-glycosides molecular scaffolds using a catalytic amount of indium trichloride (InCl₃) in good yields at room temperature. This method emphasizes inherited stereo diversity and a wide substrate scope, which enables the synthesis of various new 2-deoxy 3-bisindolyl-<i>C</i>-glycoside analogues, paving the way for further exploration of their application in medicinal chemistry and chemical biology.