Photochemical Synthesis Of Nepetanudone

Nepetanudone and nepetaparnone have been suspected of being the products of a photochemical dimerization of nepetapyrone. Both are natural products found in a variety of Nepeta species. The synthesis of (+/-)-nepetapyrone and subsequent photochemical experiments are described. (+/-)-Nepetanudone was produced upon irradiation of (+/-)-nepetapyrone, while (+/-)-nepetaparnone, a diastereomer of nepetanudone, was not observed.