Second-generation synthesis of (-)-viriditoxin

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

Research output: Contribution to journalArticle

11 Citations (Scopus)

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

Fingerprint

Ruthenium
Dimerization
Aspergillus
Tubulin
Metabolites
Biological Products
Anions
Negative ions
Monomers
viriditoxin
Trace metals

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry
  • Catalysis

Cite this

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

Second-generation synthesis of (-)-viriditoxin. / Grove, Charles I.; Fettinger, James C.; Shaw, Jared T.

In: Synthesis, Vol. 44, No. 3, Z105311SS, 2012, p. 362-371.

Research output: Contribution to journalArticle

Grove, CI, Fettinger, JC & Shaw, JT 2012, 'Second-generation synthesis of (-)-viriditoxin', Synthesis, vol. 44, no. 3, Z105311SS, pp. 362-371. https://doi.org/10.1055/s-0031-1289651
Grove CI, Fettinger JC, Shaw JT. Second-generation synthesis of (-)-viriditoxin. Synthesis. 2012;44(3):362-371. Z105311SS. https://doi.org/10.1055/s-0031-1289651
Grove, Charles I. ; Fettinger, James C. ; Shaw, Jared T. / Second-generation synthesis of (-)-viriditoxin. In: Synthesis. 2012 ; Vol. 44, No. 3. pp. 362-371.
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