Second-Generation Synthesis of (-)-Viriditoxin
- Synthesis (Stuttg). 2012;2012(3):362-371. doi: 10.1055/s-0031-1289651.
Affiliations
- 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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