Towards the Synthesis of Thiotetronic Acids Found in Groundwater and the Synthesis and Reactions of New 1,4-Oxathiin-S,S-dioxides

Sing, Matthew
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University of Guelph

Project one: Recently, Gabryelski and co-workers identified naturally occurring analogues of thiolactomycin located in groundwater samples. These compounds have not been previously characterized, making identification difficult. To accomplish full elucidation of these thiotetronic acids (TA), as well as providing access to new synthetic analogues, we have established a new synthetic method; allowing the successful synthesis of a TA. Project two: Extending previously explored chemistry from the Schwan group, a series of 1,4-oxathiin-S,S-dioxides were produced. Using a series of 5-(2-iodo-phenyl)-6-aryl-substituted-1,4-oxathiin-S,S-dioxides, Heck cross-coupling reactions were carried out. A separate selection of 1,4-oxathiins were subjected to iron(III) chloride, which was found as a facile method of ring opening. Two 1,4-oxathiin systems were tested in a series of base catalyzed reactions, and their ultimate stereochemistry was elucidated through a newly devised racemization method. Computational calculations were carried out on several pathways to further the understanding of how the stereochemical outcome might be achieved.

Thiotetronic Acids, Groundwater, 1,4-Oxathiin