The Wieland–Miescher ketone[2] is a racemic bicyclic diketone (enedione) and is a versatile synthon which has so far been employed in the total synthesis of more than 50 natural products, predominantly sesquiterpenoids, diterpenes and steroids possessing possible biological properties including anticancer, antimicrobial, antiviral, antineurodegenerative and immunomodulatory activities.

Examples of syntheses performed using the optically active enantiomer of this diketone as a starting material are that of ancistrofuran[3] and the Danishefsky total synthesis of Taxol.

An enantioselective synthesis employs L-proline as an organocatalyst:[7] This reaction was reported in 1971 by Z. G. Hajos and D. R. Parrish.

In their patent, the isolation and characterization of the above pictured optically active intermediate bicyclic ketol (in parentheses) has also been described, because they worked at ambient temperature in anhydrous dimethylformamide (DMF) solvent.

[9] This reaction has also been performed in a one-pot procedure, leading to 49% yield and 76% enantiomeric excess (ee):[10] Other proline-based catalysts have been investigated.