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.

Cite this paper

@article{Grove2012SecondGenerationSO, title={Second-Generation Synthesis of (-)-Viriditoxin.}, author={Charles I. Grove and Jared T Shaw}, journal={Synthesis}, year={2012}, volume={2012 3}, pages={362-371} }