The Diels-Alder reactions of 4-acetoxy-2-cyclopenten-1-one and 2-bromo-4-acetoxy-2-cyclopenten-1-one with vinylarenes are discussed. The aromatization of the reaction product opens a new two- step route for the synthesis of cyclopentaphenanthrenones. Structure analysis of reaction products by H-1 and C-13-NMR spectroscopy is reported.