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Highly Selective Synthesis of Halomon, Plocamenone, and Isoplocamenone.

ABSTRACT: 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.

SUBMITTER: Bucher C

PROVIDER: S-EPMC4634703 | biostudies-literature | 2015 Oct

REPOSITORIES: biostudies-literature

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Highly Selective Synthesis of Halomon, Plocamenone, and Isoplocamenone.

Bucher Cyril C Deans Richard M RM Burns Noah Z NZ

Journal of the American Chemical Society 20150929 40

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 ...[more]

PMID: 26394844

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