Ruthenium-catalyzed stereo- and chemoselective oxidative coupling of vinyl ketones: efficient access to ( E , E )-1,6-dioxo-2,4-dienes.

A Ru-catalyzed direct oxidative coupling reaction of vinyl ketones was developed. It offers a straightforward and atom-economical protocol for the synthesis of functionalized ( E , E )-1,6-dioxo-2,4-diene derivatives in moderate to good yields with excellent stereo- and chemoselectivities. In addition, the synthetic utility of this method was further demonstrated by its application to the synthesis of bioactive natural products such as (7 E ,9 E )-henicosa-7,9-diene-6,11-dione (sex pheromone), ostopanic acid (plant anticancer agent), JA (anti-tumor agent) and the southern part (C1-C13) of the antibiotic macrolactin-T.