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Bacterial Toxins

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Synthesis and Assay of Vibrio Quorum Sensing Inhibitors

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Second-Generation Synthesis of (-)-Viriditoxin.

Charles I Grove¹, Jared T Shaw

¹Department of Chemistry, University of California, One Shields Ave, Davis, CA 95616.

|October 11, 2012

Summary

Researchers developed a scalable synthesis for viriditoxin, a natural product inhibiting bacterial FtsZ (filamenting temperature-sensitive mutant Z). This work advances the production of this potential antibacterial agent.

Area of Science:

Natural Product Synthesis
Organic Chemistry
Medicinal Chemistry

Background:

Viriditoxin is a secondary metabolite from Aspergillus viridinutans.
Viriditoxin inhibits FtsZ, a bacterial protein essential for cell division and homologous to eukaryotic tubulin.

Purpose of the Study:

To describe a streamlined, scalable, and highly diastereoselective synthesis of viriditoxin.
To report key advances in the synthesis of viriditoxin and its precursors.
To disclose a novel ruthenium-catalyzed reaction observed during the synthesis.

Main Methods:

Development of an efficient synthesis for the unsaturated pyranone precursor.
Scalable assembly of the naphthopyranone monomer.
Optimization of the biaryl-coupling reaction for improved diastereoselectivity.

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Investigation of a serendipitous ruthenium-catalyzed anion dimerization.

Main Results:

A highly diastereoselective and scalable synthetic route to viriditoxin was established.
Key intermediates, including the unsaturated pyranone and naphthopyranone monomer, were synthesized efficiently.
The diastereoselectivity of the crucial biaryl-coupling step was significantly improved.
A novel ruthenium-catalyzed anion dimerization was discovered, arising from residual catalyst.

Conclusions:

The described synthetic strategy provides a viable and scalable method for producing viriditoxin.
This work facilitates further biological evaluation and potential development of viriditoxin as an antibacterial agent.
The discovery of the ruthenium-catalyzed dimerization offers new insights into catalytic reactions.