2. Academic Validation
  3. Second-Generation Synthesis of (-)-Viriditoxin

Second-Generation Synthesis of (-)-Viriditoxin

  • Synthesis (Stuttg). 2012;2012(3):362-371. doi: 10.1055/s-0031-1289651.
Charles I Grove 1,  Jared T Shaw
Affiliations

Affiliation

  • 1 Department of Chemistry, University of California, One Shields Ave, Davis, CA 95616.
PMID: 23049144 DOI: 10.1055/s-0031-1289651
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.

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