Recent advances in the stereoselective synthesis of isoprostanes and neuroprostanes.

This review delineates several reported methods for the synthesis of isoprostanes and neuroprostanes with particular emphasis on the stereocontrolled construction of a suitably functionalized cyclopentane core. The alpha- and omega-side chains of these PG-like molecules are typically assembled by Wittig-type olefination reactions, standard transformations in the PG synthesis. The synthetic strategies include free radical cyclizations, a palladium-promoted coupling of three different components, an intramolecular cyclopropanation reaction-ring-opening sequence, a [2+2] photocycloaddition-ring-opening metathesis approach, and an intramolecular cross-coupling reaction of an alkyl iodide and a tethered alkenylsiloxane.