Wikipedia:Today's featured article/February 15, 2009

The aldol reaction is an important carbon-carbon bond formation reaction in organic chemistry. In its usual form, it involves the nucleophilic addition of a ketone enolate to an aldehyde to form an aldol (β-hydroxy ketone), a structural unit found in many naturally occurring molecules and pharmaceuticals. Sometimes, the aldol addition product loses a molecule of water during the reaction to form an α,β-unsaturated ketone. This is called an aldol condensation. The aldol reaction was discovered independently by Charles-Adolphe Wurtz and by Alexander Porfyrevich Borodin in 1872. Borodin observed the aldol dimerization of 3-hydroxybutanal from acetaldehyde under acidic conditions. The aldol reaction is used widely in the large-scale production of commodity chemicals such as pentaerythritol. The aldol structural motif is especially common in polyketides, a class of natural products from which many pharmaceuticals are derived, including the potent immunosuppressant FK506, the tetracycline antibiotics, and the antifungal agent amphotericin B. Extensive research on the aldol reaction has produced highly efficient methods which enable the otherwise challenging synthesis of many polyketides in the laboratory. (more...)