Epoxidation of Protected (1,4,5)‐Cyclohex‐2‐ene‐triols and Their Acid Hydrolysis to Synthesize Quercitols from D‐(−)‐Quinic Acid

Abstract

Highly stereoselective epoxidations have been achieved in both cyclohexylidene acetal and butane 2,3‐bisacetal (BBA) protection of (1,4,5)‐cyclohex‐2‐ene‐triols. These epoxy derivatives are all derived from D‐(−)‐quinic acid and can be used for the synthesis of muco‐, (+)‐epi‐, (+)‐vibo, (−)‐talo, and (−)‐gala‐quercitols.

Keywords:

• D‐(−)‐Quinic acid
• epoxidation
• quercitol

Acknowledgment

We gratefully acknowledge the National Science Council (NSC92‐2113‐M‐032‐004) and Tamkang University for supporting this work.