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Synthesis 2012(3): 362-371
DOI: 10.1055/s-0031-1289651
DOI: 10.1055/s-0031-1289651
FEATUREARTICLE
© Georg Thieme Verlag
Stuttgart ˙ New York
Second-Generation Synthesis of (-)-Viriditoxin
Further Information
Received
8 November 2011
Publication Date:
16 January 2012 (online)
Publication History
Publication Date:
16 January 2012 (online)
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.
Key words
natural products - asymmetric synthesis - antibiotics - atropisomerism - biaryls
- Primary data for this article are available online and can be cited using the following DOI: 10.4125/pd0024th:
- Primary Data
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References
Crystallographic data for compound 9 have been submitted to Cambridge Crystallographic Database and assigned deposition number CCDC 858638.