Second-Generation Synthesis of (-)-Viriditoxin

Charles I. Grove, James C. Fettinger & Jared T. Shaw
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...

2 Related Works

CCDC 858638: Experimental Crystal Structure Determination

C.I. Grove, J.C. Fettinger & J.T. Shaw
Related Article: C.I.Grove, J.C.Fettinger, J.T.Shaw|2012|Synthesis|44|362|doi:10.1055/s-0031-1289651

Second-Generation Synthesis of (-)-Viriditoxin

Charles I. Grove, James C. Fettinger & Jared T. Shaw
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...

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