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.