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)
Pages (from-to)15515-15518
Number of pages4
JournalJournal of the American Chemical Society
Volume141
Issue number39
DOIs
StatePublished - Oct 2 2019

    Fingerprint

ASJC Scopus subject areas

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

Cite this