Journal
SYNTHESIS-STUTTGART
Volume 44, Issue 3, Pages 362-371Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0031-1289651
Keywords
natural products; asymmetric synthesis; antibiotics; atropisomerism; biaryls
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Funding
- NIH/NIAID [R01AI080931]
- NSF [CHE-0840444]
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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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