title: Second-Generation Synthesis of (-)-Viriditoxin.
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.
authors.affiliation: Department of Chemistry, University of California, One Shields Ave, Davis, CA 95616.
authors.forename: Charles I
authors.initials: CI
authors.lastname: Grove
authors.forename: Jared T
authors.initials: JT
authors.lastname: Shaw