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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 13
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Original Articles

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

Tzenge‐Lien Shih Department of Chemistry, Tamkang University, Tamsui, Taipei County, Taiwan, Republic of ChinaCorrespondence[email protected]
&
Ya‐Ling Lin Department of Chemistry, Tamkang University, Tamsui, Taipei County, Taiwan, Republic of China
Pages 1809-1817 | Received 11 Jan 2005, Published online: 15 Aug 2006
 
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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.

Acknowledgment

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

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