The asymmetric synthesis of cyclopentachromenones from gold-catalyzed reaction of readily available skipped alkenynones is described. This cascade
reaction involves an initial anti-Michael hydroarylation
of the ynone moiety to form a gold-functionalized
dialkenylketone intermediate, followed by a Nazarov
cyclization that proceeds in an unprecedented enantioselective manner. Excellent enantiomeric ratios and chemical yields are obtained under mild reaction conditions.
