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A Biomimetic Synthesis Elucidates the Origin of Preuisolactone A.

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.

SUBMITTER: Novak AJE

PROVIDER: S-EPMC7249536 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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A Biomimetic Synthesis Elucidates the Origin of Preuisolactone A.

Novak Alexander J E AJE Grigglestone Claire E CE Trauner Dirk D

Journal of the American Chemical Society 20190923 39

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. ...[more]

PMID: 31518120

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