Enantioselective total synthesis of (+)-panepophenanthrin, a novel inhibitor of the ubiquitin-activating enzyme

An enantioselective total synthesis of the novel natural product (+)-panepophenanthrin has been accomplished in which a biomimetic Diels-Alder dimerisation is a key step. The monomeric precursor 2 was assembled from the readily available Diels-Alder adduct of cyclopentadiene and p-benzoquinone through a short, simple sequence employing chemo- and stereoselective operations.