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 language | English (US) |
|---|---|
| Article number | Z105311SS |
| Pages (from-to) | 362-371 |
| Number of pages | 10 |
| Journal | Synthesis |
| Volume | 44 |
| Issue number | 3 |
| DOIs | |
| State | Published - 2012 |
Keywords
- antibiotics
- asymmetric synthesis
- atropisomerism
- biaryls
- natural products
ASJC Scopus subject areas
- Organic Chemistry
- Catalysis
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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