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■ An Efficient SeO2/FeCl3 Promoted Acylation:Intramolecular Friedel-Crafts Reaction Leading to a One-Pot Synthesis of Wrightiadione and Its Derivatives

Huan Zhang, Qi Wang, Lu Huang, Ziye Tian, Shunguang Zhang,* and Youlai Zhang*

*Tianjin Key Laboratory of Drug Targeting and Bioimaging, School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384, P.R. China.

Abstract

Wrightiadione has been shown to exhibit a broad range of biological activities. An efficient and straightforward synthetic method for generating wrightiadione and its derivatives which contain a unique tetracyclic isoflavone moiety was developed. This unprecedented one-pot route utilizes a wide spread of substrates through three-step tandem Riley oxidation/Friedel-Crafts reaction/oxidation with SeO2/FeCl3 in moderate yield.