Publications

53. Chang, C.-Y.; Aponick, A. Enantioselective Synthesis of Allylic Sulfones via Rhodium-Catalyzed Direct Hydrosulfonylation of Allenes and Alkynes. J. Am. Chem. Soc. 2024, 146, 16996–17002. DOI: 10.1021/jacs.4c05629

52. Ketelboeter, D. R.; Pappoppula, M.; Aponick, A. Chemoselective Diazine Dearomatization: The Catalytic Enantioselective Dearomatization of Pyrazine. J. Am. Chem. Soc. 2024, 146 (17), 11610–11615,  DOI: 10.1021/jacs.4c02979

51. Yin, S.; Weeks, K. N.; Aponick, A. Catalytic Enantioselective Alkyne Addition to Nitrones Enabled by Tunable Axially Chiral Imidazole-Based P,N-Ligands. J. Am. Chem. Soc. 2024, 146, 7185–7190,  DOI: 10.1021/jacs.4c00873

50. Yin, S.; Liu, J.; Weeks, K. N.; Aponick, A. Catalytic Enantioselective Synthesis of Axially Chiral Imidazoles by Cation-Directed Desymmetrization. J. Am. Chem. Soc. 2023, 145, 28176–28183,  DOI: 10.1021/jacs.3c10746

49. Pappoppula, M.; Olsen, K. L.; Ketelboeter, D. R.; Aponick, A. Enantio- and Regioselective Copper-Catalyzed 1,2-Dearomatization of Pyridines. Angew. Chem., Int. Ed. 2023, 62, e202312967. DOI: 10.1002/anie.202312967

48. Dahiya, G.; Abboud, K. A.; Aponick, A. Tuning StackPhim Ligands: Applications in Enantioselective Borylation and Alkynylation. Synthesis 2022, 54, 2157–2164. DOI: 10.1055/a-1730-2473

47. Markovic, M.; Ben-Shabat, S.; Manda, J. N.; Abramov-Harpaz, K.; Regev, C.; Miller, Y.; Aponick, A.; Zimmermann, E. M.; Dahan, A. PLA2-Triggered Activation of Cyclosporine-Phospholipid Prodrug as a Drug Targeting Approach in Inflammatory Bowel Disease Therapy. Pharmaceutics 2022, 14, 675. DOI: 10.3390/pharmaceutics14030675

46. Markovic, M.; Abramov-Harpaz, K.; Regev, C.; Ben-Shabat, S.; Aponick, A.; Zimmermann, E. M.; Miller, Y.; Dahan, A. Prodrug-Based Targeting Approach for Inflammatory Bowel Diseases Therapy: Mechanistic Study of Phospholipid-Linker-Cyclosporine PLA2-Mediated Activation. Int. J. Mol. Sci. 2022, 23, 2673. DOI: 10.3390/ijms23052673

45. Liu, J.; Laguna, E. M.; Kizhakkayil Mangadan, A. R.; Kang, K.; Aponick, A. The Enantioselective Intermolecular Saegusa Allylation. ACS Catal. 2021, 11, 14842–14847,  DOI: 10.1021/acscatal.1c04546

44. Mangadan, A. R. K.; Liu, J.; Aponick, A. Enantioselective Lactonization by π-Acid-Catalyzed Allylic Substitution: A Complement to π-Allylmetal Chemistry. Angew. Chem., Int. Ed. 2021, 60, 22224–22229. DOI: 10.1002/anie.202108336

43. Dahiya, G.; Pappoppula, M.; Aponick, A. Configuration Sampling With Five-Membered Atropisomeric P, N-Ligands. Angew. Chem., Int. Ed. 2021, 60, 19604–19608,  DOI: 10.1002/anie.202102642

42. Manda, J. N.; Butler, B. B.; Aponick, A. Synthesis and Biological Evaluation of the Southern Hemisphere of Spirastrellolide A and Analogues. J. Org. Chem. 2020, 85, 13694–13709,  DOI: 10.1021/acs.joc.0c01867

41. Manda, J. N.; Markovic, M.; Zimmermann, E. M.; Ben-Shabat, S.; Dahan, A.; Aponick, A. Phospholipid Cyclosporine Prodrugs Targeted at Inflammatory Bowel Disease (IBD) Treatment: Design, Synthesis, and in Vitro Validation. ChemMedChem 2020, 15, 1639–1644. DOI: 10.1002/cmdc.202000317

41. Markovic, M.; Ben-Shabat, S.; Aponick, A.; Zimmermann, E. M.; Dahan, A. Lipids and Lipid-Processing Pathways in Drug Delivery and Therapeutics. Int. J. Mol. Sci. 2020, 21, 3248. DOI: 10.3390/ijms21093248

40. Dahan, A.; Markovic, M.; Aponick, A.; Zimmermann, E. M.; Ben-Shabat, S. The prospects of lipidic prodrugs: an old approach with an emerging future. Future Med. Chem. 2019, 11 (19), 2563–2571,  DOI: 10.4155/fmc-2019-0155

39. Mishra, S.; Aponick, A. Lactone Synthesis by Enantioselective Orthogonal Tandem Catalysis. Angew. Chem., Int. Ed. 2019, 58, 9485–9490,  DOI: 10.1002/anie.201904438

38. DeRatt, L. G.; Pappoppula, M.; Aponick, A. A Facile Enantioselective Alkynylation of Chromones. Angew. Chem., Int. Ed. 2019, 58, 8416–8420,  DOI: 10.1002/anie.201902405

37. Markovic, M.; Ben-Shabat, S.; Keinan, S.; Aponick, A.; Zimmermann, E. M.; Dahan, A. Molecular Modeling-Guided Design of Phospholipid-Based Prodrugs. Int. J. Mol. Sci. 2019, 20, 2210. DOI: 10.3390/ijms20092210

36. Markovic, M.; Dahan, A.; Keinan, S.; Kurnikov, I.; Aponick, A.; Zimmermann, E. M.; Ben-Shabat, S. Phospholipid-Based Prodrugs for Colon-Targeted Drug Delivery: Experimental Study and In-Silico Simulations. Pharmaceutics 2019, 11, 186. DOI: 10.3390/pharmaceutics11040186

35. Markovic, M.; Ben-Shabat, S.; Keinan, S.; Aponick, A.; Zimmermann, E. M.; Dahan, A. Lipidic prodrug approach for improved oral drug delivery and therapy. Med. Res. Rev. 2019, 39 (2), 579–607,  DOI: 10.1002/med.21533

34. Liu, J.; Mishra, S.; Aponick, A. Enol Acetates: Versatile Substrates for the Enantioselective Intermolecular Tsuji Allylation. J. Am. Chem. Soc. 2018, 140, 16152–16158,  DOI: 10.1021/jacs.8b08746

33. Markovic, M.; Ben-Shabat, S.; Keinan, S.; Aponick, A.; Zimmermann, E. M.; Dahan, A. Prospects and Challenges of Phospholipid-Based Prodrugs. Pharmaceutics 2018, 10, 210. DOI: 10.3390/pharmaceutics10040210

32. Liu, J.; Miotto, R. J.; Segard, J.; Erb, A. M.; Aponick, A. Catalytic Dehydrative Lactonization of Allylic Alcohols. Org. Lett.2018, 20, 3034–3038,  DOI: 10.1021/acs.orglett.8b01063

31. Dahan, A.; Markovic, M.; Keinan, S.; Kurnikov, I.; Aponick, A.; Zimmermann, E. M.; Ben-Shabat, S. Computational Modeling and In-Vitro/In-Silico Correlation of Phospholipid-Based Prodrugs for Targeted Drug Delivery in Inflammatory Bowel Disease. J. Comput. Aided Mol. Des. 2017, 31, 1021–1028. DOI: 10.1007/s10822-017-0079-5

30. Dahan, A.; Markovic, M.; Epstein, S.; Cohen, N.; Zimmermann, E. M.; Aponick, A.; Ben-Shabat, S. Phospholipid-Drug Conjugates as a Novel Oral Drug Targeting Approach for the Treatment of Inflammatory Bowel Disease. Eur. J. Pharm. Sci.2017, 108, 78–85,  DOI: 10.1016/j.ejps.2017.06.022

29. Mishra, S.; Liu, J.; Aponick, A. Enantioselective Alkyne Conjugate Addition Enabled by Readily Tuned Atropisomeric P,N-Ligands. J. Am. Chem. Soc. 2017, 139 (9), 3352–3355,  DOI: 10.1021/jacs.7b00363

28. Paioti, P. H. S.; Abboud, K. A.; Aponick, A. Incorporation of Axial Chirality into Phosphino-Imidazoline Ligands for Enantioselective Catalysis. ACS Catal. 2017, 7, 2133–2138,  DOI: 10.1021/acscatal.7b00133

27. Dahan, A.; Ben-Shabat, S.; Cohen, N.; Keinan, S.; Kurnikov, I.; Aponick, A.; Zimmermann, E. M. Phospholipid-Based Prodrugs for Drug Targeting in Inflammatory Bowel Disease: Computational Optimization and In-Vitro Correlation Curr. Top. Med. Chem. 2016, 16, 2543–2548 DOI: 10.2174/1568026616666160414122913

26. de Oliveira Silva, J.; Angnes, R. A.; Menezes da Silva, V. H.; Servilha, B. M.; Adeel, M.; Braga, A. A. C.; Aponick, A.; Correia, C. R. D. Intermolecular Noncovalent Hydroxy-Directed Enantioselective Heck Desymmetrization of Cyclopentenol: Computationally Driven Synthesis of Highly Functionalized cis-4-Arylcyclopentenol Scaffolds. J. Org. Chem. 2016, 81, 2010–2018,  DOI: 10.1021/acs.joc.5b02846

25. Paioti, P. H. S.; Abboud, K. A.; Aponick, A. Catalytic Enantioselective Synthesis of Amino Skipped Diynes. J. Am. Chem. Soc. 2016, 138, 2150–2153. DOI: 10.1021/jacs.5b13387

24. Pappoppula, M.; Aponick, A. Enantioselective Total Synthesis of (−)-Martinellic Acid. Angew. Chem., Int. Ed. 2015, 54, 15827–15830. DOI: 10.1002/anie.201507849

23. Pappoppula, M.; Cardoso, F. S. P.; Garrett, B. O.; Aponick, A. Enantioselective Copper-Catalyzed Quinoline Alkynylation. Angew. Chem., Int. Ed. 2015, 54, 15202–15206. DOI: 10.1002/anie.201507848

22. Goodwin, J. A.; Ballesteros, C. F.; Aponick, A. Diastereoselective Synthesis of Protected 1,3-Diols by Catalytic Diol Relocation. Org. Lett. 2015, 17, 5574–5577. DOI: 10.1021/acs.orglett.5b02725

21. Butler, B. B.; Manda, J. N.; Aponick, A. Synthesis of the Spirastrellolide A, B/C Spiroketal: Enabling Solutions for Problematic Au(I)-Catalyzed Spiroketalizations. Org. Lett. 2015, 17, 1902–1905. DOI: 10.1021/acs.orglett.5b00711

20. Borrero, N. V.; DeRatt, L. G.; Barbosa, L. F.; Abboud, K. A; Aponick, A. Tandem Gold-Catalyzed Dehydrative Cyclization/Diels–Alder Reactions: Facile Access to Indolocarbazole Alkaloids. Org. Lett. 2015, 17, 1754–1757. DOI: 10.1021/acs.orglett.5b00528

19. Goodwin, J. A.; Aponick, A. Regioselectivity in the Au-Catalyzed Hydration and Hydroalkoxylation of Alkynes.
Chem. Commun. 2015, 51, 8730-8741. DOI: 10.1039/C5CC00120J

19. Paioti, P. H. S.; Ketcham, J. M.; Aponick, A. Controlling Regiochemistry in the Gold-Catalyzed Synthesis of Unsaturated Spiroketals. Org. Lett. 2014, 16, 5320–5323.

18. Kahali, B.; Marquez, S. B.; Thompson, K. W.; Yu, J.; Gramling, S. J. B.; Lu, L.; Aponick, A.; Reisman, D. Flavonoids From Each of the Six Structural Groups Reactivate BRM, a Possible Cofactor for the Anticancer Effects of Flavonoids. Carcinogenesis 2014, 35, 2183–2193. DOI: 10.1093/carcin/bgu117

17. Ketcham, J. M.; Cardoso, F. S. P.; Biannic, B.; Piras, H.; Aponick, A. Nitrogen Nucleophiles in Au-Catalyzed Dehydrative Cyclization Reactions. Isr. J. Chem. 2013, 53, 923–931. DOI: 10.1002/ijch.201300041

16. Cardoso, F. S. P.; Abboud, K. A.; Aponick, A. Design, Preparation, and Implementation of an Imidazole-Based Chiral Biaryl P,N-Ligand for Asymmetric Catalysis. J. Am. Chem. Soc. 2013, 135, 14548–14551. DOI: 10.1021/ja407689a

15. Palms, J. A.; Paioti, P. H. S.; de Souza, L. P.; Aponick, A. Pd(II)-Catalyzed Spiroketalization of Ketoallylic Diols. Chem. Eur. J. 2013, 19, 11613–11621. DOI: 10.1002/chem.201301723

14. Ghebreghiorgis, T.; Kirk, B. H.; Aponick, A.; Ess, D. H. Multiple Mechanisms in Pd(II)-Catalyzed SN2′ Reactions of Allylic Alcohols. J. Org. Chem. 2013, 78, 7664–7673. DOI: 10.1021/jo4012283

13. Ketcham, J. M.; Biannic, B.; Aponick, A. The Tandem Intermolecular Hydroalkoxylation/Claisen Rearrangement. Chem. Commun. 2013, 49, 4157–4159. DOI: 10.1039/C2CC37166A

12. Palmes, J.; Aponick, A. Strategies for Spiroketal Synthesis Based on Transition-Metal Catalysis. Synthesis 2012, 44, 3699–3721. DOI: 10.1055/s-0032-1317489

11. Borrero, N. V.; Aponick, A. Total Synthesis of Acortatarin A Using a Pd(II)-Catalyzed Spiroketalization Strategy. J. Org. Chem. 2012, 77, 8410–8416. DOI: 10.1021/jo301835e

10. Ghebreghiorgis, T.; Biannic, B.; Kirk, B. H.; Ess, D. H.; Aponick, A. The Importance of Hydrogen Bonding to Stereoselectivity and Catalyst Turnover in Gold-Catalyzed Cyclization of Monoallylic Diols. J. Am. Chem. Soc. 2012, 134, 16307–16318. DOI: 10.1021/ja306333a

9. Biannic, B.; Aponick, A. Gold-Catalyzed Dehydrative Transformations of Unsaturated Alcohols. Eur. J. Org. Chem. 2011, 2011, 6605–6617. DOI: 10.1002/ejoc.201100858

8. Biannic, B.; Ghebreghiorgis, T.; Aponick, A. A Comparative Study of the Au-Catalyzed Cyclization of Hydroxy-Substituted Allylic Alcohols and Ethers. Beilstein J. Org. Chem. 2011, 7, 802–807. DOI: 10.3762/bjoc.7.91

7. Aponick, A.; Biannic, B. Chirality Transfer in Au-Catalyzed Cyclization Reactions of Monoallylic Diols: Selective Access to Specific Enantiomers Based on Olefin Geometry. Org. Lett. 2011, 13, 1330–1333. DOI: 10.1021/ol200203k

6. Chojnacka, K.; Santoro, S.; Awartani, R.; Richards, N. G. J.; Himo, F. Aponick, A. Synthetic Studies on the Solanacol ABC Ring System by Cation-Initiated Cascade Cyclization: Implications for Strigolactone Biosynthesis. Org. Biomol. Chem. 2011, 9, 5350–5353. DOI: 10.1039/C1OB05751K

5. Aponick, A.; Biannic, B.; Jong, M. R. A Highly Adaptable Catalyst/Substrate System for the Synthesis of Substituted Chromenes. Chem. Commun. 2010, 46, 6849–6851. DOI: 10.1039/C0CC01961E

4. Aponick, A.; Li, C.-Y.; Malinge, J.; Marques, E. F. An Extremely Facile Synthesis of Furans, Pyrroles, and Thiophenes by the Dehydrative Cyclization of Propargyl Alcohols. Org. Lett. 2009, 11, 4624–4627. DOI: 10.1021/ol901901m

3. Aponick, A.; Li, C.-Y.; Palmes, J. A. Au-Catalyzed Cyclization of Monopropargylic Triols: An Expedient Synthesis of Monounsaturated Spiroketals. Org. Lett. 2009, 11, 121–124. DOI: 10.1021/ol802491m

2. Aponick, A.; Biannic, B. Gold-Catalyzed Dehydrative Cyclization of Allylic Diols. Synthesis 2008, 20, 3356–3359. DOI: 10.1055/s-0028-1083160

1. Aponick, A.; Li, C.-Y.; Biannic, B. Au-Catalyzed Cyclization of Monoallylic Diols. Org. Lett. 2008, 10, 669–671. DOI: 10.1021/ol703002p