Highly Selective Synthesis of Halomon, Plocamenone, and Isoplocamenone

Over 160 chiral vicinal bromo­chlorinated natural products have been identified; however, a lack of synthetic methods for the selective incorporation of halogens into organic molecules has hindered their synthesis. Here we disclose the first total synthesis and structural confirmation of iso­plocam­enone and plocam­enone, as well as the first selective and scalable synthesis of the preclinical anticancer natural product halomon. The synthesis of these inter-halogenated compounds has been enabled by our recently developed chemo-, regio-, and enantio­selective dihalogenation reaction.