Synthesis of a New Family of Aminocyclitols from D-(-)-Quinic Acid

Abstract

In continuation of our interest in the synthesis of glycosidase inhibitors, we report herein an efficient synthesis of three new polyhydroxylated amino cyclohexane derivatives (aminocyclitols) that may potentially possess important biological activities. The key step involved the highly stereoselective dihydroxylation of protected azido cyclohexene derivatives 5, 9, and 15, which were easily red from D-(-)-quinic acid. The subsequent hydrogenation step was conducted under acidic conditions to provide the target molecules in an efficient manner with high overall yields.

Keywords:

• Aminocyclitol
• dihydroxylation
• quinic acid

ACKNOWLEDGMENT

We gratefully acknowledge the National Science Council (NSC95-2113-M-032-004-MY3) and Tamkang University for financial support of this work. We also thank the National Center for High-Performing Computing for assistance.