Thiolactones in carbohydrate chemistry

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This research project centers around investigations of some fundamental, but as yet not studied, reactions of carbohydrate thiolactones. The project can be broken down into the following areas:1) The development of new and improved synthetic methods to carbohydrate thiolactones that will allow their facile synthesis on a multi gram scale, making them viable synthetic intermediates and amenable for further study2) Study and optimization of the reactivity of these thiolactones with a variety of alcohols, under different types of reaction conditions3) Investigation of the use of thiolactones for the total synthesis of a class of highly potent anti-fungal compounds called the Papulacandins. Analogs will also be synthesized and their biological activity tested by our collaborators.4) Investigation of some novel reduction reactions of compounds derived in section 2) above, in an attempt to open up a new way for controlling the stereochemistry of glycosylation reactions.