An expedient synthesis of spiroketals: model studies for the calylucin C16-C25 fragment

Ari Koskinen, Vesa Rauhala, Marta Nevalainen

    Research output: Contribution to journalArticleScientificpeer-review

    14 Citations (Scopus)
    31 Downloads (Pure)

    Abstract

    Anew short strategy to prepare the spiroketal fragment of calyculins is presented. A novel Seyferth–Gilbert type homologation of hindered lactols to the corresponding alkynes has been achieved for the first time. The spirocyclization was achieved efficiently via a DIHMA (double intramolecular hetero-Michael addition) process of this hindered ynone. The spirocyclization rate is not dependent on the stereochemistry of the alkoxy substituent in the oxolane ring.
    Original languageEnglish
    Pages (from-to)9199-9204
    JournalTetrahedron
    Issue number60
    Publication statusPublished - 2004
    MoE publication typeA1 Journal article-refereed

    Keywords

    • enantioselectivity
    • natural products
    • spiroketals

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