A Concise Synthesis of Pleurotin Enabled by a Nontraditional C-H Epimerization

John F. Hoskin, Erik J. Sorensen

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7 Scopus citations


An 8-step synthesis of a known pentacyclic intermediate toward the natural product pleurotin (1) is described. Pleurotin and related benzoquinone natural products are of great interest for their powerful anticancer and antibiotic activities. The route features a regio- and diastereoselective intermolecular photoenolization/Diels-Alder cycloaddition and an alkoxy-radical-induced hydrogen atom transfer-mediated C-H epimerization to construct pleurotin's carbon framework with appropriate relative stereochemical relationships. The synthesis concludes with a ring-forming benzylic C-H oxidation to deliver oxepane 19.

Original languageEnglish (US)
Pages (from-to)14042-14046
Number of pages5
JournalJournal of the American Chemical Society
Issue number31
StatePublished - Aug 10 2022

All Science Journal Classification (ASJC) codes

  • General Chemistry
  • Biochemistry
  • Catalysis
  • Colloid and Surface Chemistry


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