We gratefully acknowledge the The NSF (CAREER 1844443; 2019 – 2024) and the NIH (R35 GM137893-01; 2020 – 2025) for funding many aspects of our research program!Publications: 28. Three-Component cine,ipso-Disubstitution of Nitrocoumarins Vincent Vedovato, Anghelo J. Gangano, Ion Ghiviriga, and Alexander J. Grenning* Org. Lett. 2024, 26, 3, 647–652 27. Axially Chiral Cannabinoids: Design, Synthesis, and Cannabinoid Receptor Affinity Sara E. Kearney, Anghelo J. Gangano, Primali V. Navaratne, Daniel G. Barrus, Kyle J. Rehrauer, Terry-Elinor R. Reid, Adrian Roitberg, Ion Ghiviriga, Christopher W. Cunningham*, Thomas Gamage*, and Alexander J. Grenning*ChemRxiv preprint HERE. J. Am. Chem. Soc. 2023, 145, 13581–13591 26. Altered methionine metabolism impacts phenylpropanoid production and plant development in Arabidopsis thaliana Doosan Shin, Veronica C. Perez, Gabriella K. Dickinson, Haohao Zhao, Ru Dai, Breanna Tomiczek, Keun Ho Cho, Ning Zhu, Jin Koh, Alexander Grenning, Jeongim Kim* The Plant Journal, In Press 25. Vicinal Stereocenters via Asymmetric Allylic Alkylation and Cope rearrangement; A Straightforward Route to Functionally and Stereochemically Rich Heterocycles Aleksandra Nilova,† Michael D. Mannchen,† Abdias N. Noel, Evgeniy Semenova, and Alexander J. Grenning*† Equal contribution. These authors reserve the right to list their names first. Chem. Sci., 2023, 14, 2755-2762 24. Diastereoselective Indole-Dearomative Cope Rearrangements by Compounding Minor Driving Forces Subhadip De, Breanna M. Tomiczek, Yinuo Yang, Kenneth Ko, Ion Ghiviriga, Adrian Roitberg*, and Alexander J. Grenning*ChemRxiv preprint HERE. Org. Lett. 2022, 24, 20, 3726 23. Construction of vicinal 4°/3°-carbons via reductive Cope rearrangement. Kristin M. Sobie, Matthew Albritton, Yinuo Yang, Mariana M. Alves, Adrian Roitberg*, and Alexander J. Grenning*ChemRxiv preprint HERE. Chem. Sci., 2022, 13, 1951-1956 22. 1,2,4-Trifunctionalized Cyclohexane Synthesis via a Diastereoselective Reductive Cope Rearrangement and Functional Group Interconversion Strategy. Michael D. Mannchen, Ion Ghiviriga, Khalil A. Abboud, and Alexander J. Grenning* Org. Lett. 2021, 23, 8804–8809 21. [3,3] Ring Rearrangement of Oxo- or Aza-Bridged Bicyclo[3.2.1]octene-Based 1,5-Dienes. Evgeniya Semenova, Ouidad Lahtigui, Ion Ghiviriga, and Alexander J. Grenning* Org. Lett. 2021, 23, 2263–2267 20. Aromatic Cope rearrangements Breanna M. Tomiczeka and Alexander J. Grenning* Org. Biomol. Chem. 2021, 19, 2385-2398 19. Function‐oriented and modular (+/–)‐cis‐pseudoguaianolide synthesis: Discovery of new Nrf2 Activators and NF‐κB Inhibitors Fabien Emmetiere, Ranjala Ratnayake, Henry A. M. Schares, Katherine F. M. Jones, Emily Bevan-Smith, Hendrik Luesch,* Daniel A. Harki,* and Alexander J. Grenning* Chem. Eur. J. 2021, 27, 5564. 18. Overcoming Kinetic and Thermodynamic Challenges of Classic Cope Rearrangements Ehsan Fereyduni, Ouidad Lahtigui, Jacob N. Sanders, Breanna M. Tomiczek, Michael D. Mannchen, Roland A. Yu, K. N. Houk,* and Alexander J. Grenning,* J. Org. Chem. 2021, 86, 2632–2643. 17. Selective ring-rearrangement or ring-closing metathesis of bicyclo[3.2.1]octenes E. Semenova, O. Lahtigui, S. Scott, M. Albritton, K. A. Abboud, I. Ghiviriga, A. E. Roitberg* and A. Grenning* Chem. Commun., 2020, 56, 11779-11782. 16. Functional Group Interconversion of Alkylidenemalononitriles to Primary Alcohols by a Cooperative Redox Operation F. Emmetiere, A. J. Grenning Synthesis. 2020, 52(20), 3077-3085 15. Axially‐Chiral Cannabinols: A New Platform for Cannabinoid‐Inspired Drug Discovery Primali V. Navaratne, Jenny L. Wilkerson, Kavindri D. Ranasinghe, Evgeniya Semenova, Jasmine S. Felix, Lance R. McMahon, Adrian Roitberg, Ion Ghiviriga, and Alexander J. Grenning* ChemMedChem, 2020, 15, 728–732. 14. Diastereoselective Synthesis of 2,3,4-Trisubstituted Tetrahydrofurans via Thermally Reactive 1,5-Diene-tert-butyl Carbonates Fabien Emmetiere and Alexander J. Grenning Org. Lett. 2020, 22, 842 13. Promoting Thermodynamically Unfavorable [3,3] Rearrangements by Chemoselective Reduction Vertesaljai, P.; Serrano, R.; Mannchen, M. D.; Williams, M.; Semenova, E.; Grenning, A. J. Org. Lett., 2019, 21, 5704–5707 12. Accessing the decarboxylative allylation–divinylcyclopropane-cycloheptadiene rearrangement from the ketone/aldehyde substrate pool Schroeder, R.; Grenning, A. J. Tetrahedron, 2019, 75, 3231 11. Controlling, Understanding, and Redirecting the Thermal Rearrangement of 3,3-Dicyano-1,5-enynes Scott, S. K.; Sanders, J. N.; White, K. E.; Yu, R. A.; Houk, K. N.; Grenning, A. J. J. Am. Chem. Soc., 2018, 140, 16134 10. Transient [3,3] Cope rearrangement of 3,3-dicyano-1,5-dienes: computational analysis and 2-step synthesis of arylcycloheptanes Ehsan Fereyduni, Jacob N. Sanders, Gabriel Gonzalez, K. N. Houk*, and Alexander J. Grenning* Chem. Sci., 2018, 9, 8760 9. Tetrahydrobenzochromene Synthesis Enabled by a Deconjugative Alkylation/Tsuji-Saegusa-Ito Oxidation on Knoevenagel Adducts Navaratne, P. V.; Grenning, A. J. Org. Lett., 2018, 20, 4566 8. Complex Hydroindoles by an Intramolecular Nitrile-Intercepted Allylic Alkylation Cascade Reaction Vertesaljai, P.; Ghiviriga, I.; Grenning, A. J. Org. Lett., 2018, 20, 1970-1973 7. Factors Governing and Application of the Cope Rearrangement of 3,3-Dicyano-1,5-dienes and Related Studies Fereyduni, E.; Grenning, A. J. Org. Lett., 2017, 19, 4130 6. An Enyne Cope Rearrangement Enables Polycycloalkane Synthesis from Abundant Starting Materials by a Simple Strategy Scott, Sarah K. ; Grenning, A. J. Angew. Chem. Int. Ed., 2017, 56, 8125 5. Simplifying Complex Scaffold Synthesis: Knoevenagel Adduct Allyl Anions as Easily Generated Multifunctional Reagents Grenning, A. J. Synlett, 2017, 28, 633 4. A Deconjugative Alkylation/Diels-Alder Cycloaddition Strategy to Synthesize 2-Substituted Bicyclic Scaffolds Zhang,; W.; Ghiviriga, I.; Grenning, A. J. Tetrahedron, 2017, 73, 4076 3. Deconjugative Alkylation/ “Pairing” as a Simple Platform for Carbocycle Synthesis Navaratne, P. V.; Grenning, A. J. Org. Biomol. Chem., 2017, 15, 69-75 2. Assembly of Terpenoid Cores by a Simple Tunable Strategy Lahtigui, O.; Emmetiere, F.; Zhang, W.; Jirmo, L.; Toledo-Roy, S.; Hershberger, J. C.; Grenning, A. J. Angew. Chem. Int. Ed., 2016, 55, 15792 –15796 1. Knoevenagel Adducts as Trimethylenemethane Dipole Surrogates Vertesaljai, P.; Navaratne, P. V.; Grenning, A. J. Angew. Chem. Int. Ed., 2016, 55, 317