Ontology highlight
ABSTRACT:
SUBMITTER: Novak AJE
PROVIDER: S-EPMC7249536 | biostudies-literature | 2019 Oct
REPOSITORIES: biostudies-literature
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]