New Chemical Tools for the Synthesis of Sesquiterpenes Natural Products.
Sesquiterpene lactones are a family of natural products that have been found to have anti-tumor, anti-bacterial and anti-inflammatory properties. As molecules with potential therapeutic benefit, there is a great deal of interest in finding new ways to generate these molecules synthetically, as their abundance in nature can be very low. In this project, we investigated the use of silylglyoxylates as precursors to these natural products. Silylglyoxylates are an underutilized class of molecules that can be photochemically activated to generate carbenes. Carbenes are reactive chemical intermediates that have the ability to undergo a C-H insertion reaction and form a five-membered lactone, which is the key structural element of a sesquiterpene lactone. In this experiment, phenethyl (tert-butyldimethyl)silylglyoxylate was converted into a carbene using photochemical activation with a 254 nm lamp. The progress of the reaction was monitored by nuclear magnetic resonance spectroscopy, thin layer chromatography and column chromatography. Initial results suggest this molecule is a promising candidate to form a carbon-carbon bond under our reaction conditions. Overall, if our silylglyoxylate precursor is successful in forming this carbon-carbon bond, it will lead the way in replacing other existing methods or carbene formation, which are not amenable to large-scale synthesis.
Faculty Mentor: Tina Bott