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Synthesis 2012(3): 362-371  
DOI: 10.1055/s-0031-1289651
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart ˙ New York

Second-Generation Synthesis of (-)-Viriditoxin

Charles I. Grove, James C. Fettinger, Jared T. Shaw*
Department of Chemistry, University of California, One Shields Ave, Davis, CA 95616, USA
e-Mail: jtshaw@ucdavis.edu;
Further Information

Publication History

Received 8 November 2011
Publication Date:
16 January 2012 (online)

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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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Crystallographic data for compound 9 have been submitted to Cambridge Crystallographic Database and assigned deposition number CCDC 858638.