Charles Bessey Professor
Hamilton Hall 809B/829
402.472.6951
dussault@unlserve.unl.edu

Dussault Research Group
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Current research in the Dussault group focuses on several related areas:

1) Organic synthesis

2) New oxidation methods

3) Chemistry of peroxide explosives

4) Chemical biology

Organic Synthesis:
Peroxide natural products: There are very few synthetic methods with which to approach the growing number of peroxide-containing natural products. Our group is a leader in the development of new methods for peroxide synthesis, as illustrated by the first syntheses of plakinic acids (J. Org. Chem. 2006, 71, 2283) and the peroxyacarnoates (Org. Lett. 2005, 7, 2509). Current research explores organometallic approaches to the peroxyplakorates.

Antimalarials: Peroxides are of interest as therapeutic agents for drug-resistant malaria. As part of a collaboration with Prof. Jon Vennerstrom (UNMC) and the Swiss Tropical Institute, we recently discovered that spiro-bisperoxyketals are stable and easily prepared compounds demonstrating promising activity in antimalarial assays (Org. Lett., 2008, 10, 2401).

New Oxidation Chemistry:
Although alkene ozonolysis has been known for over a century, we have discovered that the “textbook” chemistry of the intermediate carbonyl oxides can be strongly perturbed by the presence of Lewis acids and/or nucleophiles, offering a significant expansion in the utility of this oxidation, a process requiring only oxygen and electricity. (J. Org. Chem. 2008, 73, 4688); Tetrahedron, 2006, 62, 10747) Outgrowths of this project resulted in the discovery of the Re(VII)-catalyzed synthesis of 1,1-dihydroperoxides and 1,2,4,5-tetraoxanes; the latter are of major interest as potential antimalarials. (Org. Lett., 2008 10, 4577)

Peroxide explosives:
Triacetone triperoxide (TATP) is an easily prepared explosive of great concern as a weapon of terrorism. As part of a DoD-funded collaboration with five other departmental research groups, we are investigating the fundamental chemistry of TATP and related compounds in order to determine improved conditions for their detection and decomposition.

Chemical Biology:
A long-term collaboration with Prof. Ken Nickerson (UNL School of Biological Sciences) uncovered the first examples of fungal quorum sensing, in which a released chemical signal (farnesol) controls population dependent cell-cell communication. Ongoing efforts in this area seek to explore the therapeutic consequences of synthetic enhancement of or interference with this pathway. (Bioorg. Med. Chem. 2008, 16, 1842) A collaboration with Prof. Tim Carr (UNL Nutrition Sciences) is exploring the relationship of molecular structure with dietary uptake and processing of plant sterols (J. Nutr. 2006, 136, 2722). Other ongoing collaborations target the preparation of bacterial quorum sensing molecules, enzyme inhibitors, and unnatural fatty acids.