A chemoenzymatic synthesis of the cis-decalin core associated with the novel anti-mitotic agent phomopsidin: Some observations concerning a high-pressure-promoted diels-alder cycloaddition reaction of (1S,2R)-3-methyl-cis-1,2-dihydrocatechol and the anionic oxy-cope rearrangement of compounds derived from the adduct

Martin G. Banwell*, Alison J. Edwards, Malcolm D. McLeod, Scott G. Stewart

*Corresponding author for this work

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    16 Citations (Scopus)

    Abstract

    The enantiomerically pure and enzymatically derived cis-1,2-dihydrocatechol 2 engages in a diastereofacially selective Diels-Alder cycloaddition reaction with commercially available lactone 3 at 19 kbar to afford adduct 4, which is readily elaborated to the diene-ol 13. Treatment of this last compound with KH/18 [crown]-6 resulted in successive anionic oxy-Cope and 1,2-Wittig rearrangements to afford acyloin 14 embodying the cis-decalin core associated with the natural product phomopsidin (1). Compound 16 also engages in an anionic oxy-Cope rearrangement reaction to give, depending on the molar equivalents of base used, either the cis-decalin 17 or the hexahydroindene 18. The structure of compound 18 has been established by single-crystal X-ray diffraction analysis.

    Original languageEnglish
    Pages (from-to)641-644
    Number of pages4
    JournalAustralian Journal of Chemistry
    Volume57
    Issue number7
    DOIs
    Publication statusPublished - 2004

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