European Journal of Organic Chemistry 2018-02-21

Total Synthesis of Catunaregin and Preliminary Evaluation of its Antitumor Activity

Hideki Abe; Takuma Hikichi; Kosuke Emori; Akihito Yokosuka; Yoshihiro Mimaki; Toyoharu Kobayashi; Hisanaka Ito

Index: 10.1002/ejoc.201800219

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Abstract

Total synthesis of catunaregin in both racemic and optically active forms was accomplished. This enantioselective synthesis employs Evans aldol methodology using oxazolidinone or thiazolidinethione as the chiral auxiliary. The key features include a syn selective aldol reaction to form the Evans‐syn or Non‐Evans‐syn product, and successive ketalization of a furanyl diol derivative under acidic conditions. The biological properties of the synthetic racemate and both enantiomers were evaluated against A549 and HL‐60 human cancer cells.