Synthetic studies on phloroglucins: a new approach to the bicyclo[3.3.1]nonane system via the regioselective ring-opening of the methoxycyclopropane

Masahito Abe, Masahisa Nakada

    Research output: Contribution to journalArticle

    25 Citations (Scopus)

    Abstract

    A new synthetic approach to the bicyclo[3.3.1]nonane system, a common structure in a number of polyisoprenylated phloroglucinol derivatives (phloroglucins), has been developed. The key step in our approach is a 'one-pot' procedure of two successive reactions, the intramolecular cyclopropanation reaction which affords the tricyclo[4.4.0.05,7]dec-2-ene derivative and its methoxy group directed regioselective ring-opening reaction mediated by ZnCl2, producing the desired bicyclo[3.3.1]nonane as the sole product.

    Original languageEnglish
    Pages (from-to)4873-4877
    Number of pages5
    JournalTetrahedron Letters
    Volume48
    Issue number28
    DOIs
    Publication statusPublished - 2007 Jul 9

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    Phloroglucinol
    Derivatives
    bicyclo(3.3.1)nonane

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

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    abstract = "A new synthetic approach to the bicyclo[3.3.1]nonane system, a common structure in a number of polyisoprenylated phloroglucinol derivatives (phloroglucins), has been developed. The key step in our approach is a 'one-pot' procedure of two successive reactions, the intramolecular cyclopropanation reaction which affords the tricyclo[4.4.0.05,7]dec-2-ene derivative and its methoxy group directed regioselective ring-opening reaction mediated by ZnCl2, producing the desired bicyclo[3.3.1]nonane as the sole product.",
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