The Diels-Alder reaction of juglone with various styrenes in the presence of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) was promoted by B(OAc)(3) at room temperature. The reaction proceeded smoothly and gave the products in a good yield and with excellent regioselectivity. This strategy was applied to the total syntheses of tetrangulol and anhydrolandomycinone.

The first total syntheses of (±)-parimycin and (R)-parimycin were accomplished from O-methylnaphthazarin (6) in nine synthetic steps. Intermolecular Diels−Alder reaction of 6 with diene 7, cyclodehydrogenation catalyzed by iodinedimethyl sulfoxide, and sodium dithionite reduction were the key steps. The absolute configuration of natural parimycin was determined to be S.

The asymmetric total syntheses of (+)-5-epi-schisansphenin B and the proposed structure of (+)-15-hydroxyacora-4(14),8-diene have been accomplished from 1,3-cyclopentadione (10) in eight synthetic steps. The enantioselective palladium-catalyzed redox-relay Heck alkenylation, the intramolecular Stetter reaction, and the regioselective Tiffeneau–Demjanov-type ring expansion were the pivotal steps in these syntheses.

The title reaction is generally carried out in the presence of excess alkene and reagents to provide a simple approach to benzanthracenequinone derivatives.