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Synthesis and chemical diversity analysis of bicyclo[3.3.1]non-3-en-2-ones.

ABSTRACT: Functionalized bicyclo[3.3.1]non-3-en-2-ones are obtained from commercially available phenols by a hypervalent iodine oxidation, enone epoxidation, epoxide thiolysis, and intramolecular aldol reaction sequence. Reaction optimization studies identified room temperature as well as microwave-mediated procedures, providing moderate to good yields (57%-88%) in the thiophenol-mediated epoxide opening and intramolecular aldol reaction. In addition, the isolation of a key intermediate and in situ NMR studies supported the mechanistic hypothesis. The bicyclic ring products occupy novel chemical space according to ChemGPS and Chemaxon chemical diversity and cheminformatics analyses.

SUBMITTER: Hammill JT

PROVIDER: S-EPMC2925319 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature

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Synthesis and chemical diversity analysis of bicyclo[3.3.1]non-3-en-2-ones.

Hammill Jared T JT Contreras-García Julia J Virshup Aaron M AM Beratan David D Yang Weitao W Wipf Peter P

Tetrahedron 20100301 31

Functionalized bicyclo[3.3.1]non-3-en-2-ones are obtained from commercially available phenols by a hypervalent iodine oxidation, enone epoxidation, epoxide thiolysis, and intramolecular aldol reaction sequence. Reaction optimization studies identified room temperature as well as microwave-mediated procedures, providing moderate to good yields (57%-88%) in the thiophenol-mediated epoxide opening and intramolecular aldol reaction. In addition, the isolation of a key intermediate and in situ NMR st ...[more]

PMID: 20798897

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