Stereoselective synthesis of the C13-32 spiroacetal fragment of spirangien A

Claire Gregg, Michael Perkins

    Research output: Contribution to journalArticlepeer-review

    3 Citations (Scopus)

    Abstract

    Stereoselective synthesis of an advanced intermediate towards the highly cytotoxic polyketide metabolite spirangien A was achieved. A key step in the synthesis was installation of the C23 stereocentre by a substrate controlled C22-23 aldol reaction. Comparison of this result with previous literature reports suggests that the facial preference of the aldehyde controls the outcome of the C22-23 aldol coupling and depends on the O27/25 protecting groups when reacting with complex ketones, which contain the C17-15 stereochemistry.

    Original languageEnglish
    Pages (from-to)6845-6854
    Number of pages10
    JournalTetrahedron
    Volume69
    Issue number33
    DOIs
    Publication statusPublished - 19 Aug 2013

    Keywords

    • Aldol reaction
    • Cytotoxic
    • Polyketide
    • Spirangien
    • Spiroacetal

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