Regioselectivity in the Ring Opening of Epoxides for the Synthesis of Aminocyclitols from D-(-)-Quinic Acid

Abstract

Efficient syntheses of four aminocyclitols are reported. Each synthesis is accomplished in eight steps starting from D-(-)-quinic acid. The key step involves a highly regioselective ring opening of epoxides by sodium azide.

Keywords

• aminocyclitols
• epoxides
• glycosidase inhibitors
• D-(-)-quinic acid
• regioselective ring opening