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Synthesis 2009(20): 3383-3390  
DOI: 10.1055/s-0029-1216981
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Synthesis of (+)- and (-)-Wuweizisu C Stereoisomers and Their Chemosensitizing Effects on Multidrug-Resistant Cancer Cells

Yanfeng Lia, Qiang Wangb, Lihong Dongc, Xiaohe Guoc, Wei Wanga, Jingxi Xieb, Junbiao Chang*a,b
a College of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China
b Department of Chemistry, Zhengzhou University, Zhengzhou 450001, P. R. of China
Fax: +86(371)87783017; e-Mail: changjunbiao@zzu.edu.cn;
c Henan Key Laboratory of Fine Chemicals, Henan Academy of Sciences, Zhengzhou 450001, P. R. of China
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Publication History

Received 12 May 2009
Publication Date:
28 August 2009 (online)

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Abstract

Total syntheses of the dibenzocyclooctadiene natural product wuweizisu C in its (-)-form [(S)-1] and its (+)-form [(R)-1] were achieved in 19 steps, starting from commercially available gallic acid. In the key step, the asymmetric biphenyl axis was constructed by an oxazoline-mediated Ullmann reaction to provide either the P or M biaryl product in 68% yield and >99% de, depending on the configuration of the oxazoline. The efficiency of this total synthesis was excellent, as the syntheses of (S)-1 and (R)-1 from intermediate 7 each proceeded in 13 steps with an overall yield of 6.8%. (S)-1 and (R)-1 were evaluated as chemosensitizers for multidrug-resistant cancers.

Key words

wuweizisu C - stereoisomer - asymmetric synthesis - biaryls - multidrug resistance - p-glycoprotein