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*

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.

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*

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.

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.

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.

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*

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*

20. Aromatic Cope rearrangements

Breanna M. Tomiczeka and Alexander J. Grenning*

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*

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,*

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*

16. Functional Group Interconversion of Alkylidenemalononitriles to Primary Alcohols by a Cooperative Redox Operation

F. Emmetiere, A. J. Grenning

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*

14. Diastereoselective Synthesis of 2,3,4-Trisubstituted Tetrahydrofurans via Thermally Reactive 1,5-Diene-tert-butyl Carbonates

Fabien Emmetiere and Alexander J. Grenning

13. Promoting Thermodynamically Unfavorable [3,3] Rearrangements by Chemoselective Reduction

Vertesaljai, P.; Serrano, R.; Mannchen, M. D.; Williams, M.; Semenova, E.; Grenning, A. J.

12. Accessing the decarboxylative allylation–divinylcyclopropane-cycloheptadiene rearrangement from the ketone/aldehyde substrate pool

Schroeder, R.; Grenning, A. J.

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.

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*

9. Tetrahydrobenzochromene Synthesis Enabled by a Deconjugative Alkylation/Tsuji-Saegusa-Ito Oxidation on Knoevenagel Adducts

Navaratne, P. V.; Grenning, A. J.

8. Complex Hydroindoles by an Intramolecular Nitrile-Intercepted Allylic Alkylation Cascade Reaction

Vertesaljai, P.; Ghiviriga, I.; Grenning, A. J.

7. Factors Governing and Application of the Cope Rearrangement of 3,3-Dicyano-1,5-dienes and Related Studies

Fereyduni, E.; Grenning, A. J.

6. An Enyne Cope Rearrangement Enables Polycycloalkane Synthesis from Abundant Starting Materials by a Simple Strategy

Scott, Sarah K. ; Grenning, A. J.

5. Simplifying Complex Scaffold Synthesis: Knoevenagel Adduct Allyl Anions as Easily Generated Multifunctional Reagents

Grenning, A. J.

4. A Deconjugative Alkylation/Diels-Alder Cycloaddition Strategy to Synthesize 2-Substituted Bicyclic Scaffolds

Zhang,; W.; Ghiviriga, I.; Grenning, A. J.

3. Deconjugative Alkylation/ “Pairing” as a Simple Platform for Carbocycle Synthesis

Navaratne, P. V.; Grenning, A. J.

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.

1. Knoevenagel Adducts as Trimethylenemethane Dipole Surrogates

Vertesaljai, P.; Navaratne, P. V.; Grenning, A. J.