Second-generation synthesis of (-)-viriditoxin

Charles I. Grove, James C. Fettinger, Jared T. Shaw

Research output: Contribution to journalArticlepeer-review

13 Scopus citations


Viriditoxin is a secondary metabolite isolated from Aspergillus viridinutans that has been shown to inhibit FtsZ, the bacterial homologue of eukaryotic tubulin. A streamlined, scalable, and highly diastereoselective synthesis of this complex natural product is described. Key advances include a more efficient synthesis of the requisite unsaturated pyranone, scalable assembly of the naphthopyranone monomer, and improved diastereoselectivity in the biaryl-coupling reaction. In addition, we disclose a serendipitous ruthenium-catalyzed anion dimerization resulting from trace metal left by an RCM reaction.

Original languageEnglish (US)
Article numberZ105311SS
Pages (from-to)362-371
Number of pages10
Issue number3
StatePublished - 2012


  • antibiotics
  • asymmetric synthesis
  • atropisomerism
  • biaryls
  • natural products

ASJC Scopus subject areas

  • Organic Chemistry
  • Catalysis


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