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https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/f7b1cebc-7d1a-4375-acf4-423686f96a1b/11_2021_Michael_PaperOL.png News and Updates https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/ff49203a-2305-47ab-811d-79d6475a8ac5/10_2021_AkashAndJuan.png News and Updates https://www.grenninglab.com/contact daily 0.75 2024-02-01 https://www.grenninglab.com/research-summaries daily 0.75 2021-11-19 https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/f8744bd0-546f-475d-aab3-a428935eadec/Cope+Rearrangement.png Research Summaries - The Cope rearrangement! We are developing a platform for chemical synthesis centered about a classic transformation The project encompasses many of the hallmarks of organic synthesis; methods development, physical organic chemistry, computational chemistry, target synthesis (natural and unnatural products), and collaborative drug discovery. https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/e09aa231-b1a1-45c5-8da8-1f532fb2c659/axCBNs.png Research Summaries - Axially-chiral cannabinols! We are developing a new class of cannabinoid for applications in drug discovery. We have hypothesized that axially-chiral-cannabinols (ax-CBNs), unnatural and unknown isomers of cannabinol (CBN), may be valuable scaffolds for cannabinoid-inspired drug discovery. There are two main factors directing our interest to these scaffolds: (a) ax-CBNs would have ground-state three-dimensionality; ligand–receptor interactions can be more significant with complimentary 3D-topology, and (b) ax-CBNs at their core sare biaryl molecules, generally attractive platforms for pharmaceutical development due to their ease of functionalization and stability . https://www.grenninglab.com/publications daily 0.75 2026-04-07 https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/02219d9a-7614-48b6-aa00-2633e9ced700/TOC_PTDISNAR.png Publications - 33. a-Aryl-a-Heteroarylmalononitriles via Proton-Transfer Dual-Ionization Nucleophilic Aromatic Substitution Avneesh Kumar, Akash Gogate, Alexander Grenning* https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/38c9025e-3617-46c0-8441-6588e9f0f70d/Screenshot+2025-12-18+at+3.12.39%E2%80%AFPM.png Publications - 32. 3-Azetidinylpiperidine-4-Alkylidenemalononitrile and Related Building Blocks Juan Sanfiel, Andrew T. McCabe, Aleksandra Nilova, Samuel L. Graf, and Alexander J. Grenning* https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/8bdc803f-eccf-4359-bcf5-0e2faf39df83/Screenshot+2025-12-17+at+3.13.50%E2%80%AFPM.png Publications - 31. C3 Stereogenic- or Quaternary- Carbon Quinolones via Heteroaromatic Claisen Rearrangement Akash R. Gogate, Morgane Mando, Andrew T. McCabe, Geeta Kumari, Pallavi Singh, Alexandra E. Ramirez, Choukri Ben Mamoun,* and Alexander J. Grenning* in collaboration with GK, PS, CBM; Yale University, Yale School of Medicine https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/95da0626-cc05-4a58-927a-64e02945582f/BisCF3+Social+Media.png Publications - 30. Synthesis of 1,3-bis-trifluoromethylated-(hetero)cyclohexane-2-carboxylates from alkylidenemalononitriles Morgane Mando, Dylan J. Smith, Jan-Niklas Boyn,* and Alexander J. Grenning* ChemRxiv link HERE. https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/8acc5c27-275b-47de-8223-768e87c6463d/TOC_June.png Publications - 29. Teaching an Old Dog New Tricks for Achieving CB2-Selective Inverse Agonism Morgane Mando, Christopher W. Cunningham , and Alexander J. Grenning * https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/abae1d43-a7fe-44bf-acb3-3a7bb93b0297/OL.png Publications - 28. Three-Component cine,ipso-Disubstitution of Nitrocoumarins Vincent Vedovato, Anghelo J. Gangano, Ion Ghiviriga, and Alexander J. Grenning* https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/19540bcf-b9a1-486f-a597-9423022100a5/axCannabinoidTOC.png Publications - 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. https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/697aaca9-55b7-4cb7-ad29-4015eea3b515/Picture1.png Publications - 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* https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/957aba32-f2b1-4cca-b4e2-dd4051847edc/ChemSci.png Publications - 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. https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/29885fff-1c11-4f63-be91-6ca2f48d8042/Dearomative+Cope+TOC.png Publications - 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. https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/d2c86b64-a2b8-4243-b2c6-410f95c28a55/ChemSciTOC.png Publications - 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. https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/807a9476-0e50-41a1-bb11-293f78460efe/OL_2021png.png Publications - 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* https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/f13db3b9-2403-4454-9543-c72be56de681/Org+Lett+2.png Publications - 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* https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/8e071ca6-517c-4d6f-9e88-d942ac055f75/OBC_1.png Publications - 20. Aromatic Cope rearrangements Breanna M. Tomiczeka and Alexander J. Grenning* https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/6828da9f-82b3-4f42-8a80-62d84d8dd061/ChemEurJ_1.png Publications - 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* https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/f704e995-6a59-493e-8bf1-d930a1714539/JOC_1.png Publications - 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,* https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/52d339c1-1a1b-4bd6-8546-da760441c925/ChemCommun_1.png Publications - 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* https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/24f04b28-0004-4d7b-83d2-23b7a80bdb37/Synlett.png Publications - 16. Functional Group Interconversion of Alkylidenemalononitriles to Primary Alcohols by a Cooperative Redox Operation F. Emmetiere, A. J. Grenning https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/479a3970-3cd9-4ecd-9953-8cdd5972ebd4/ChemMedChem.png Publications - 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* https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/48e84331-35c3-4978-9f69-b9563575c3d2/OL_1.png Publications - 14. Diastereoselective Synthesis of 2,3,4-Trisubstituted Tetrahydrofurans via Thermally Reactive 1,5-Diene-tert-butyl Carbonates Fabien Emmetiere and Alexander J. Grenning https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/60c3c46d-7285-4db0-af7e-de4b4a1a0661/OL1.png Publications - 13. Promoting Thermodynamically Unfavorable [3,3] Rearrangements by Chemoselective Reduction Vertesaljai, P.; Serrano, R.; Mannchen, M. D.; Williams, M.; Semenova, E.; Grenning, A. J. https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/cfd99ab4-670a-48b2-9bb2-b31aed6032de/Tetrahedron.png Publications - 12. Accessing the decarboxylative allylation–divinylcyclopropane-cycloheptadiene rearrangement from the ketone/aldehyde substrate pool Schroeder, R.; Grenning, A. J. https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/3f1b230d-fc9e-42f8-9746-57dc7dd01325/JACS.png Publications - 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. https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/cdd651b6-6abf-40bd-bba2-5a2d89eae68a/ChemSci.png Publications - 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* https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/bd14ea5b-0737-4c10-8180-ff8def2a289d/OL1.png Publications - 9. Tetrahydrobenzochromene Synthesis Enabled by a Deconjugative Alkylation/Tsuji-Saegusa-Ito Oxidation on Knoevenagel Adducts Navaratne, P. V.; Grenning, A. J. https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/02a75a7b-a08b-40bd-b6fc-096d93c55bdb/OL2.png Publications - 8. Complex Hydroindoles by an Intramolecular Nitrile-Intercepted Allylic Alkylation Cascade Reaction Vertesaljai, P.; Ghiviriga, I.; Grenning, A. J. https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/0abb0c48-95fe-4cb0-9e98-5b3436880f93/OL1.png Publications - 7. Factors Governing and Application of the Cope Rearrangement of 3,3-Dicyano-1,5-dienes and Related Studies Fereyduni, E.; Grenning, A. J. https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/2e67267a-91d7-4ba7-b5da-1fe609adb863/ACIEE1.png Publications - 6. An Enyne Cope Rearrangement Enables Polycycloalkane Synthesis from Abundant Starting Materials by a Simple Strategy Scott, Sarah K. ; Grenning, A. J. https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/415ceffe-092c-4945-b695-0f7c50bd8c71/Synlett.png Publications - 5. Simplifying Complex Scaffold Synthesis: Knoevenagel Adduct Allyl Anions as Easily Generated Multifunctional Reagents Grenning, A. J. https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/d774655b-654e-4e46-b2c3-f38c0fdc4415/Tetrahedron.png Publications - 4. A Deconjugative Alkylation/Diels-Alder Cycloaddition Strategy to Synthesize 2-Substituted Bicyclic Scaffolds Zhang,; W.; Ghiviriga, I.; Grenning, A. J. https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/d6c63233-3d6b-4313-b196-20e92f8fe4e5/OBC1.png Publications - 3. Deconjugative Alkylation/ “Pairing” as a Simple Platform for Carbocycle Synthesis Navaratne, P. V.; Grenning, A. J. https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/48f64e38-b519-4fd3-a93a-d8d43d6f643c/ACIEE1.png Publications - 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. https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/0d51b879-a61a-417f-9ef0-ee4915cb73af/ACIEE2.png Publications - 1. Knoevenagel Adducts as Trimethylenemethane Dipole Surrogates Vertesaljai, P.; Navaratne, P. V.; Grenning, A. J. https://www.grenninglab.com/the-team daily 0.75 2026-04-07 https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/a10d7c7a-8671-4959-942b-e257b652740c/Subhadip.png The Team! https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/72441a10-dcaf-4854-b135-2c383767ef02/Andy.png The Team! https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/c0e12570-a656-49fa-8d32-e10ae472f41d/Juan.png The Team! https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/5f26838a-56f3-43e7-b71b-dd98c4101df7/Akash.png The Team! https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/08c84844-1477-4656-acf6-cf6502af768f/Dylan.png The Team! https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/d3f65f28-2eed-4dd6-8c90-3d0318b2df29/Avneesh.png The Team! https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/c59aee24-6247-41c4-9df7-2b7c3cee88c1/Brenna.png The Team! https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/858cf69e-0f42-422e-88c0-e1b94ed047cf/Fatima.png The Team! https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/c10eaf01-930a-40ef-b2a1-d10c0bb3ec8e/Evelyn.png The Team! https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/ada432bc-4063-4f4d-95d0-673304d4b6d8/Max.png The Team! https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/79e273e5-6d75-4b9f-8e55-490be3e28a93/Alex.png https://www.grenninglab.com/moleculart daily 0.75 2025-03-14 https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/e95ced17-e027-46ff-b8c2-3b25f8fbedd9/Skatole.png MoleculArt This molecule is ! Well found in it at least (and quite pungent!). https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/aca282e0-aefd-4239-80c7-9ecd141507e8/StackPhos.png MoleculArt StackPhos is a pretty cool P,N-ligand developed by the Aponick Lab at UF. This is my take on it (with artistic liberties of course!) https://pubs.acs.org/doi/abs/10.1021/ja407689a https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/df6c13ed-6c5f-4282-88a8-4aab7d546b5a/ChairTS.png MoleculArt https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/1642462911098-YQLBEZGYMGGCNZX6MIJY/axCBN.jpg MoleculArt One of our research directions is aimed at synthesizing axially chiral cannabinoids. Here is one take on their structure! read about axCBNs here: ChemMedChem 2020, 15, 728. https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/ea74ff31-bdab-48a0-9a51-0af25f320b4f/pi_stack.png MoleculArt Paracyclophane is a very interesing three-dimensional molecule! https://images.squarespace-cdn.com/content/v1/61968b4883d7c14541408900/5009763d-05dd-4623-a2c3-b403a2feeed3/Mechanisms.jpg MoleculArt Reaction Arrorws - 1