Natural Products Inspired Organic Synthesis: An Enduring Platform for Training Next Generation Scientists
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WHERE ARE THEY (FORMER GROUP MEMBERS) NOW? Link
NATURAL PRODUCTS INSPIRED ORGANIC SYNTHESIS
The main objective of our research is to construct novel heterocyclic scaffolds via cycloadditions that would not be readily accessible otherwise and eventually utilize these new heterocycles toward biological problems. Specifically, variants of oxidopyrylium-alkene [5+2] cycloadditions are utilized to construct unique polycyclic ethers and Diels-Alder [4+2] cycloadditions of deactivated dienes are employed to construct isoindolinone derivatives. These cycloadditions are inspired by and directed toward the total synthesis of natural products.
PUBLICATIONS
Corrie, S. I.; Pearce, A. C.; Grabowski, J .P.; Randolph, K. A.; Guo, W.; Tantillo, D. J.; Mitchell, T. A. Boron-tethered oxidopyrylium-based [5+2] cycloadditions. Tetrahedron Lett. 2022, 107, 154094. https://www.sciencedirect.com/science/article/abs/pii/S0040403922005561?via%3Dihub
Singh, S.; Grabowski, J. P.; Pohani, S.; Apuzzo, C. F.; Platt, D. C.; Jones, M. A.; Mitchell, T. A. Synthesis of Polycyclic Ether-Benzopyrans and In Vitro Inhibitory Activity against Leishmania tarentolae. Molecules, 2020, 25, 5461. Link
Rokey, S. N.; Simanis, J. A.; Law, C. M.; Pohani, S.; Behrends, S. W.; Bulandr, J. J.; Ferrence, G. M.; Goodell, J. R.; Mitchell, T. A. Intramolecular asymmetric oxidopyrylium-based [5 + 2] cycloadditions. Tetrahedron Lett. 2020, 61, 152377. Link
Grabowski, J. P.; Ferrence, G. M.; Mitchell, T. A. Efforts toward the total synthesis of (±)-toxicodenane A utilizing an oxidopyrylium-based [5 + 2] cycloaddition of a silicon-tethered BOC-pyranone. Tetrahedron Lett. 2020, 61, 152324. Link
Bulandr, J. J.; Grabowski, J. P.; Law, C. M.; Shaw, J. L.; Goodell, J. R.; Mitchell, T. A. Investigation of Transfer Group, Tether Proximity and Alkene Substitution for Intramolecular Silyloxypyrone-Based [5 + 2] Cycloadditions. J. Org. Chem. 2019, 84, 10306-10320. Link
Kaufman, R. H; Law, C. M.; Simanis, J. A.; Woodall, E. L.; Zwick, C. R.; Wedler, H. B.; Wendleboe, P.; Hamaker, C. H.; Goodell, J. R.; Tantillo, D. J.; Mitchell, T. A. Oxidopyrylium-Alkene [5 + 2] Cycloaddition Conjugate Addition Cascade (C3) Sequences: Scope, Limitation, and Computational Investigations. J. Org. Chem. 2018, 83, 9318-9338. Link
Olson, C. A.; Shaner, C. E.; Roche, S. C.; Ferrence, G. M.; Mitchell, T. A. Hexahydro-1H-Isoindolinone-Like Scaffolds from Electronically Deactivated and Sterically Hindered Dienes; Synthesis in the Context of Muironolide A. Synthesis 2015, 47, 2756-2766. Link
Simanis, J. A.; Zwick, C. R.; Woodall, E. L.; Goodell, J. R. Mitchell, T. A. Further Investigation of Pyranone Activation. Heterocycles 2015, 91, 149-156. Link
Simanis, J. A.; Law, C. M.; Woodall, E. L.; Hamaker, C. G.; Goodell, J. R.; Mitchell, T. A. Investigation of Oxidopyrylium-Alkene [5+2] Cycloaddition Conjugate Addition Cascade (C3) Sequences. Chem. Commun. 2014, 50, 9130-9133. Link
Shaner, C. E.; Ferrence, G. M.; Mitchell, T. A. Synthetic Efforts toward the Isoindolinone Core of Muironolide A. Synlett 2013, 24, 1861-1864. Link
Woodall, E. L; Simanis, J. A.; Hamaker, C. G.; Goodell, J. R.; Mitchell, T. A. Unique Reactivity of anti– and syn-Acetoxypyranones en Route to Oxidopyrylium Intermediates Leading to a Cascade Process. Org. Lett. 2013, 15, 3270-3273. Link
EXTERNAL GRANTS AWARDED
National Science Foundation – Chemical Synthesis – RUI (2020-2023)
National Science Foundation – Chemical Synthesis – RUI (2016-2020)
National Science Foundation – Major Research Instrumentation (2013-2016)
Cottrell College Science Award – Research Corporation for Science Advancement (2012-2015)
Undergraduate New Investigator Grant – ACS Petroleum Research Fund (2012-2015)
RECENT NEWS
Congratulations to Sarita, Jake, and Shilpa for their paper in Molecules! 11-21-20
Congratulations to Sammi R, Justin, Marshall, Shilpa, Sammi W, Jacob, and John for their paper in Tet. Lett.! 8-26-20
Congratulations to Jake for his paper in Tet. Lett.! 8-16-20
Congratulations to Jacob, Jake, Marshall, Jess, and John, for their recent paper in JOC! 8-1-19
Congratulations to Riley, Marshall, Justin, Erica, Christian, and John, in collaboration with the Tantillo group, for their recent paper in JOC! 7-12-18
Congratulations to Vishnu, Jade, Clare, Jacob, Jessica, Jake, Declan, Keya, Priya, Isaac, Sunny, Yesha, Blake, Meghan, Lucas, and Margaret for graduating from the Illinois Summer Research Academy! 6-30-18 link
Congratulations to Jake Grabowski for receiving a Summer Undergraduate Research Fellowship from the ACS Division of Organic Chemistry! 6-4-18 link
Congratulations to Riley Kaufman and Jess Shaw who graduated with B.S. (Chemistry) in May 2018!
Congratulations to Jack, Samaya, Lauren, Malia, Brittany, Tyler, Jaeho, Apoorv, Antonio, Akhila, Bhavana, Noah, Naomi, Jack, Elisa, Dilan, Rebecca, Lucas for graduating from the Illinois Summer Research Academy! 6-30-17 link
The group was recently awarded a grant from the National Science Foundation! 9-1-16
Congratulations to Sanketh, Anna, Aditi, Tom, Josh, Adrian, and Maya for graduating from the Illinois Summer Research Academy! 7-15-16 link
Congratulations to Sammi Willens who graduate with her B.S. (Biology) in May 2016!
Congratulations to Marshall Law for successfully defending his thesis! 7-23-15
Congratulations to Jasmine, Katya, Laina, Camille, Jessica, and Alexandra for graduating from the Illinois Summer Research Academy! 6-26-15
Congratulations to Christian Zwick who graduated with his B.S. (Chemistry) in May 2015!
Congratulations to Brendan Thompson who graduated with his B.S. (Chemistry) in May 2015!
Congratulations to Stacie Cler who graduated with her B.S. (Chemistry) in May 2015!
Congratulations to Justin, Christian, Marshall, Erica, and John for their recent paper in Heterocycles! 1-15-15
Congratulations to Chris Olson who graduated with his B.S. (Chemistry) in December 2014!
Congratulations to Greg, Alexandria, Jason, Robert, and Kevin for graduating from the Illinois Summer Research Academy! 7-18-14
Congratulations to Justin, Marshall, Erica, and John for their recent paper in ChemComm! 7-3-14
Congratulations to Justin Simanis for successfully defending his M.S. thesis! 6-16-14
Congratulations to Marshall Law who graduated with his B.S. (Biochemistry) in December 2013!
Congratulations to Erica Woodall for successfully defending her M. S. thesis! 10-14-13
Congratulations to Courtnay for her recent paper in Synlett! 7-10-13
Congratulations to Erica, Justin, and John for their recent paper in Organic Letters! 6-21-13
Congratulations to Erin Mortimer who graduated with her B.S. (Biology) in May 2013!
Congratulations to Sydney Roche who graduated with her B.S. (Biochemistry) in May 2013!
Congratulations to Patrick Leszczynski who graduated with his B.S. (Chemistry) in December 2012!
Congratulations to Courtnay Shaner for successfully defending her M.S. thesis! 9-20-12
The group was recently awarded a Cottrell College Science Award from the Research Corporation for Scientific Advancement! 7-1-12
The group was recently awarded a Petroleum Research Fund – Undergraduate New Investigator Award from the American Chemical Society! 9-1-12
Congratulations to Justin Simanis who graduated with his B.S. (Chemistry) in May 2012!
Congratulations to Dave Ferge who graduated with his B.A. (English) in May 2012!
Congratulations to Louis Bajek who graduated with his B.S. (Chemistry) in May 2011!
Congratulations to Matt Beio who graduated with his B.S. (Biochemistry) in May 2011!