Second-generation synthesis of (-)-viriditoxin

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

Research output: Contribution to journalArticle

11 Scopus citations

Abstract

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
JournalSynthesis
Volume44
Issue number3
DOIs
StatePublished - 2012

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry
  • Catalysis

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    Grove, C. I., Fettinger, J. C., & Shaw, J. T. (2012). Second-generation synthesis of (-)-viriditoxin. Synthesis, 44(3), 362-371. [Z105311SS]. https://doi.org/10.1055/s-0031-1289651