AI Article Synopsis
- The synthesis of preuisolactone A is achieved using a biomimetic approach, featuring a series of key chemical reactions including a purpurogallin-type cycloaddition and fragmentation.
- This process involves additional steps such as vinylogous aldol addition, oxidative lactonization, and a benzilic acid rearrangement to complete the synthesis.
- The study clarifies that preuisolactone A is found as a racemate and proposes that it should be classified as a phenolic polyketide rather than a sesquiterpenoid.
Article Abstract
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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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7249536 | PMC |
| http://dx.doi.org/10.1021/jacs.9b08892 | DOI Listing |
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