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) |
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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