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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 17
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Original Articles

Asymmetric Synthesis of β‐DDB Through Oxazoline‐Mediated Ullmann Coupling

, , , , &
Pages 2289-2296 | Received 22 Apr 2005, Published online: 18 Aug 2006
 

Abstract

Biphenyl lignan (β‐DDB) (2), an effective drug in the treatment of hepatitis, was for the first time asymmetrically synthesized via a chiral oxazoline mediated Ullmann coupling. The two enantiomers of β‐DDB have been obtained in this way by using the optically pure amino alcohols L‐valinol and D‐valinol, respectively. However, attempts to synthesize enantiopure α‐DDB (1) by the same method failed because of the racemization of 1 at room temperature in solution.

Acknowledgment

We are grateful to the Natural Science Foundation of Anhui Province of China for financial support.

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