A Biomimetic Synthesis Elucidates the Origin of Preuisolactone A
A short, biomimetic synthesis of the fungal metabolite preuisolactone A is described. Its key steps are a purpurogallin-type (5 + 2)-cycloaddition, followed by fragmentation, vinylogous aldol addition, oxidative lactonization, and a final benzilic acid rearrangement. Our work explains why preuisolac...
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| Veröffentlicht in: | Journal of the American Chemical Society 2019-10, Vol.141 (39), p.15515-15518 |
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| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
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| Zusammenfassung: | A short, biomimetic synthesis of the fungal metabolite preuisolactone A is described. Its key steps are a purpurogallin-type (5 + 2)-cycloaddition, followed by fragmentation, vinylogous aldol addition, oxidative lactonization, and a final benzilic acid rearrangement. Our work explains why preuisolactone A has been isolated as a racemate and suggests that the natural product is not a sesquiterpenoid but a phenolic polyketide. |
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| ISSN: | 0002-7863 1520-5126 |
| DOI: | 10.1021/jacs.9b08892 |