Synthesis of DEFG ring system of cneorins

Ari M.P. Koskinen, Ainoliisa J. Pihko

    Research output: Contribution to journalArticleScientificpeer-review

    3 Citations (Scopus)
    74 Downloads (Pure)

    Abstract

    The cneorins have been isolated from the xerophytic shrub Cneorum pulverulentum, which is native to the Canary Islands. They are natural products containing a [4.3.1]propellane ring system (DEFG rings) as the northern part of the molecule and a 5,5-spiroketal unit and a butenolide moiety (A ring) as the southern part. The synthesis of the DEFG ring system of the cneorins is described. The key steps include: intramolecular cyclopropanation of a diazomalonate providing the EFG ring fragment and an anionic cyclization of a sulfone yielding the [4.3.1]propellane ring system.
    Original languageEnglish
    Pages (from-to)20-35
    JournalArkivoc
    DOIs
    Publication statusPublished - 2008
    MoE publication typeA1 Journal article-refereed

    Keywords

    • total synthesis
    • natural products
    • cneorins
    • intramolecular cyclopropanation of diazomalonates

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