University of Wisconsin - Green Bay


Research Council

Research
Success

Julie Wondergem

Julie Wondergem

Spring 2014

"Research in Organic Synthesis"

Grant in Aid of Research

Final Report: "During the 2014-2016 school years, 9 students and I continued working toward the synthesis of obolactone. The students earned a combined total of 16 independent study / research credits. They learned to run reactions, how to purify the products using column chromatography, and to characterize the new compounds they created with spectroscopic instruments.

The main focus of our work this year was on the preparation of a siloxy triene (1) compound. This requires a series of two reaction steps. The first reaction creates a second carbon-carbon double bond and a ketone product. Choice of base was shown to be critical in achieving good results. We tried bases of various strengths including, sodium hydride, triethyl amine, sodium hydroxide, DABCO (diazabicyclooctane), and DBU (diazabicycloundecene). The best results have been achieved with DBU. Then we tried varying the concentration of the base. We ran the reaction with 1 equivalent of DBU and 2 equivalents of DBU. We found that 2 equivalents of DBU gave phenomenal results. We can consistently achieve a yield of 98%! We have spectral data of both proton NMR and GC/MS which have confirmed the identity of the ketone product (2).

The second step of this synthesis creates a siloxy ether and third carbon-carbon double bond (1). Again, many reaction conditions were employed to try to form this product. Notably we initially proposed trimethylsilyl triflate (TMS) could be used to trap the enol. However, this reagent didn’t make a product that was stable enough for us to isolate and work with. We currently believe that triethylsilyl triflate (TES) does create a stable product. We are now working on isolating it and getting spectral data to prove we have made the siloxy triene (1). This siloxy triene is an important piece in the total synthesis of Obolactone. Our proposed synthesis requires a total of least 11 steps. With the work on these reactions, we are 2 steps closer to completing our total synthesis of obolactone. Our work will continue with new students, next year."


Spring 2012

"Pharmaceutical Research"

Grant in Aid of Research

Final Report: "Funding from the UWGB Research Council has allowed me to buy chemicals and glassware for 28 undergraduate students to learn to do research in organic chemistry and to earn 80 independent research credits."


Spring 2011

"Synthesis of Obolactone"

Grant for Integrating Research and Teaching


Fall 2010

"Development of a Cancer Medication"

Grant in Aid of Research


Spring 2009

"Synthesis of Obolactone"

Grant for Integrating Research and Teaching


Spring 2008

"Synthesis of Obolactone"

Grant for Integrating Research and Teaching


Spring 2007

"Synthesis of Obolactone, Part 2"

Grant for Integrating Research and Teaching


Spring 2006

"Participation of undergraduate students in preparing synthetic obolactone"

Grant for Integrating Research and Teaching


Spring 2006

"Purchase Chemicals to Prepare Catalysts"

Grant in Aid of Research