Complex Natural Products Derived from Pyrogallols

Alexander J.E. Novak, Dirk Trauner

Research output: Contribution to journalArticlepeer-review

Abstract

Pyrogallols (1,2,3-trihydroxybenzenes) are abundant in Nature, easily oxidized, and are central precursors to important natural products. The rich chemistry of their oxidized derivatives, the hydroxy-o-quinones, has been studied for over a century and still attracts the interest of the scientific community. Only in the last ten years have critical insights of pyrogallol chemistry from the mid-twentieth century been applied to modern natural product synthesis. Historical studies of pyrogallol chemistry, including [5+2], [4+2], and formal [5+5] cycloadditions are discussed here and reactivity guidelines established. The application and remarkable selectivity of these cycloadditions is then showcased in the recent syntheses of several fungal natural products, including dibefurin, epicolactone, the merocytochalasans, and preuisolactone A. The authors hope that this contribution will spark further interest in the fascinating chemistry of pyrogallols and natural products derived from them.

Original languageEnglish (US)
Pages (from-to)1-46
Number of pages46
JournalProgress in the chemistry of organic natural products
Volume118
DOIs
StatePublished - 2022

Keywords

  • Cascades
  • Cycloadditions
  • Fungal metabolites
  • o-Quinones
  • Pyrogallols
  • Racemic natural products

ASJC Scopus subject areas

  • Medicine(all)

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