Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 39, Pages 15515-15518Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b08892
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Funding
- New York University
- National Institutes of Health [R01GM126228]
- National Science Foundation through REU Site for Chemical Biology at New York University [CHE-1659619]
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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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