A biomimetic cascade for the formation of the methyl [2(5H)-furanylidene]ethanoate core of spongosoritin A and the gracilioethers

Matthew Norris, Michael Perkins

    Research output: Contribution to journalArticle

    9 Citations (Scopus)

    Abstract

    The polyketide secondary metabolites spongosoritin A and gracilioethers A-C contain a unique methyl [2(5H)-furanylidene]ethanoate core. A synthetic model of a suspected biosynthetic intermediate to these natural products was constructed in seven steps and 48% overall yield. This model undergoes a facile cyclisation/double dehydration cascade to give the desired furanylidene motif, with the required (2Z) isomer obtained in >90 dr when an ethyl substituent is located at C3′ of the furanylidene.

    Original languageEnglish
    Pages (from-to)9813-9818
    Number of pages6
    JournalTetrahedron
    Volume69
    Issue number46
    DOIs
    Publication statusPublished - 18 Nov 2013

    Keywords

    • Cyclisation/dehydration cascade
    • Gracilioether
    • Methyl [2(5H)-furanylidene]ethanoate
    • Sodio-lithio dianion enolate

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