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.