A Biomimetic Synthesis Elucidates the Origin of Preuisolactone A

Alexander J.E. Novak, Claire E. Grigglestone, Dirk Trauner

Research output: Contribution to journalArticle

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.

Original languageEnglish (US)
JournalJournal of the American Chemical Society
DOIs
StateAccepted/In press - Jan 1 2019

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Polyketides
Biomimetics
Cycloaddition
Cycloaddition Reaction
Metabolites
Biological Products
Acids
3-hydroxybutanal
purpurogallin

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

A Biomimetic Synthesis Elucidates the Origin of Preuisolactone A. / Novak, Alexander J.E.; Grigglestone, Claire E.; Trauner, Dirk.

In: Journal of the American Chemical Society, 01.01.2019.

Research output: Contribution to journalArticle

Novak, Alexander J.E. ; Grigglestone, Claire E. ; Trauner, Dirk. / A Biomimetic Synthesis Elucidates the Origin of Preuisolactone A. In: Journal of the American Chemical Society. 2019.
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