Full Publications List

Mon, 01 Jan 2024 00:00:00 +0000

65. Jakskowski, L. N; Clanton, N. A; Wilkinson, N. J; Bartels, J. L; LoCoco, P. M; Frantz, A. N; Boyer, A. D; Boerma J. W; Bush, J. E; Brown, S. D; Fernandez, K; Archer, N. E; Tekin, V; Fernandez, S. R; Risinger, A. L; Frantz, D. E; Lapi, S. E. “Pharmacokinetic and Biodistribution Studies of [18F]-Taccalonolide: A Covalent Microtubule Stabilizer with Antitumor Efficacy.” ACS Med. Chem. Lett. 2025, 16, 8, 1569–1574.

64. Wilson, N. A; Palmer, Slimp, M. K; W. M; Simmons, E. M; Joannou, M. V; Albaneze-Walker, J; Ganley, J. M; Frantz, D. E. “Ni-Catalyzed Cyanation of (Hetero)Aryl Electrophiles Using the Nontoxic Cyanating Reagent K4[Fe(CN)6].” ACS Catal. 2025, 15, 8, 6459–6465

63. Wilson, N. A; Palmer, W. M; Ganley, J. M; Coombs, J. R; Levorse, M, S; Albaneze-Walker, J; Frantz, D. E. “Palladium-Catalyzed Cyanations of Aryl Imidazolylsulfonates with K4[Fe(CN)6]: A Pragmatic Approach to Benzonitriles from Phenols.” Synthesis 2024; 56(17): 2655-2662.

61. Clanton, N.A.; Wilson, N.A.; Ortiz, E.; Blumberg, S.T.; Frantz, D.E. “Site-Selective Functionalization of Unactivated Allylic C–H Bonds via Direct Deprotonation with KTMP: Application to the Formal Total Synthesis of (+)-Artemisinin from Amorphadiene.” Org. Lett., 2023 25 (1), 277-281.

60. Cadena, M.; Villatoro, R.S.; Gupta, J.S.; Phillips, C.; Allen, J.B.; Arman, H.D.; Wherritt, D.J.; Clanton, N.A.; Ruchelman, A.L.; Simmons, E.M.; DelMonte, A.J.; Coombs, J.R.; Frantz, D.E. “Pd-Catalyzed Chemoselective O-Benzylation of Ambident 2-Quinolinone Nucleophiles.” ACS Catal. 2022, 12 (16), 10199-10206. (Highlighted in Synfacts)

59. Clanton, N.A.; Spiller, T.E.; Ortiz, E.; Frantz, D.E.; et. al. “A Metal-Free Reductive N-Alkylation of Indoles with Aldehydes.” Org. Lett., 2021, 23, 9, 3233-3236. (Highlighted as a Supplementary Cover)

58. Schneider, J.A.; Frantz, D.E.; et. al. “Disregulated Ribonucleoprotein Granules Promote Cardiomyopathy in RBM20 Gene-Edited Pigs.” NatureMedicine, 2020, 26, 1788-1800.

57. Clanton, N.A.; Hastings, S.D.; Foultz, G.B.; Contreras, J.A.; Yee, S.S.; Arman, H.D.; Risinger, A.L.; Frantz, D.E. “Synthesis and Biological Evaluations of Electrophilic Steroids Inspired by the Taccalonolides.” ACS Med. Chem. Lett. 2020, 11, 2534-2543. (Highlighted as a Supplementary Cover)

56. Munteanu, C. Spiller, T.E.; Qiu, J. DelMonte, A.J.; Wisniewski, S.R.; Simmons, E.M.; Frantz, D.E. “Pd- and Ni-Based Systems for the Catalytic Borylation of Aryl (Pseudo)halides with B 2(OH) 4.” J. Org. Chem. 2020, 85, 10334-10349. (Highlighted as a Featured Article)

55. Du, L.; Munteanu, C.; King, J.B.; Frantz, D.E.; Cichewicz, R.H. “An Electrophilic Natural Product Provides a Safe and Robust Odor Neutralization Approach to Counteract Malodorous Organosulfur Metabolites Encountered in Skunk Spray.” J. Nat. Prod.2019, 82, 1989-1999. (Also Highlighted in August 5, 2019 Issue of C&E News)

54. Neff, R.K.; Frantz, D.E. “Cationic Alkynyl Heck Reaction toward Substituted Allenes Using BobCat: A New Hybrid Pd(0)-Catalyst Incorporating a Water-Soluble dba Ligand” J. Am. Chem. Soc. 2018, 50, 17428-17432.

53. Stevens, J.M.; Parra Rivera, A.C.; Dixon, D.D.; Beutner, G.L.; Delmonte, A.; Frantz D.E.; Janey, J.M.; Paulson, J.; Talley, M. “Direct Lewis Acid-Catalyzed Conversion of Enantioenriched N-Acyloxazolidinones to Chiral Esters, Amides and Acids.” J. Org. Chem. 2018, 83, 14245-14261. (Highlighted as a Featured Article)

52. El Arba, M.; Dibrell, S.E.; Meece. F.; Frantz, D.E. “Ru(II)-Catalyzed Synthesis of Substituted Furans and Their Conversion to Butenolides” Org. Lett. 2018, 20, 5886-5888.

51. El Arba, M.; Dibrell, S.E.; Crouch, I.T.; Frantz, D.E. “Unified Approach to Substituted Allenoates via Pd-Catalyzed β-Hydride Elimination of ( E)-Enol Triflates” Org. Lett.2017, 19, 5446-5449.

50. Munteanu, C.; Frantz, D.E. “Palladium-Catalyzed Synthesis of Alkynes via a Tandem Decarboxylation/Elimination of ( E)-Enol Triflates” Org. Lett. 2016, 18, 3937-3939.

49. Parra Rivera, A.C.; Still, R.; Frantz, D.E. “Iron-Catalyzed Stereoselective Cross-Coupling Reactions of Stereodefined Enol Carbamates with Grignard Reagents.” Angew. Chem. Int. Ed. 2016, 55, 6689.

48. Neff, R.K.; Frantz, D.E. “Recent applications of chiral allenes in axial-to-central chirality transfer reactions.” Tetrahedron, 2015 71, 7-18.

47. Peniche, A.G.; Osorio, Y.; Renslo, A.R.; Frantz, D.E.; Melby, P.C.; Travi, B.L. “Development of an ex vivo lymph node explant model for identification of novel molecules active against Leishmania major.” Antimicrobial Agents and Chemotherapy 2014, 58, 78.

46. Neff, R.K.; Frantz, D.E. “Recent advances in the catalytic syntheses of allenes: A critical assessment.” ACS Catalysis 2014, 4, 519-528. (Invited Review)

45. Valentim, C.L.L.; Cioli, D.; Chevalier, R.D.; Cao, X.; Taylor, A.B.; Holloway, S.P.; Pica-mattoccia, L.; Guidi, A.; Basso, A.; Tsai, I.T.; Berriman, M.; Carvalho-Queirox, C.; Almeida, M.; Aguilar, H.A.; Frantz, D.E.; Hart, P.J.; LoVerde, P.T.; Anderson, T.J.C. “Genetic and molecular basis of drug resistance and species-specific drug action in Schistosome parasites.” Science 2013, 342, 1385-1389.

44. Risinger, A.L.; Peng, J.; Rohena, C.C.; Aguilar, H.A.; Frantz, D.E.; Mooberry, S.L. “The Bat Flower: A source of microtubule-destabilizing and –stabilizing compounds with synergistic antiproliferative actions.” J. Nat. Prod. 2013, 76, 1923-1929.

43. Wang, L; Chang, J.; Varghese, D.; Dellinger, M.; Kumar, S.; Best, A.M.; Ruiz, J.; Bruick, R.; Peña-Llopis, S.; Xu, J.; Babinski, D.J.; Frantz, D.E.; Brekken, R.A.; Quinn, A.M.; Simeonov, A.; Easmon, J.; Martinez, E.D. “A small molecule modulates Jumonji histone demethylase activity and selectively inhibits cancer growth” Nat. Commun. 2013, 4, 2035.

42. Crouch, I.T.; Neff, R.K.; Frantz, D.E. “Pd-Catalyzed Asymmetric Beta-Hydride Elimination En Route to Chiral Allenes” J. Am. Chem. Soc. 2013, 135 (13), 4970–4973. (Highlighted in the April 1issue of Chemical and Engineering News; Highlighted by Synfacts)

41. Scheuermann, T.H.; Li, Q.; Ma, H.–W.; Key, J.; Zhang, L.; Chen, R.; Garcia, J.A.; Naidoo, J.; Longgood, J.; Frantz, D.E.; Tambar, U.K.; Gardner, K.H.; Bruick, R.K. “Allosteric Inhibition of Hypoxia Inducible Factor 2 with Small Molecules” Nature Chem. Bio., 2013, 9, 271–276.

40. Rogers, J.L.; Bayeh, L.; Scheuermann, T.H.; Longgood, J.; Caldwell, C.; Key, J.; Naidoo, J.; Melito, L.; Shokri, C.; Frantz, D.E.; Bruick, R.K.; Gardner, K.H.; MacMillan, J.B.; Tambar, U.K. “Development of Inhibitors of the PAS-B Domain of the HIF-2α Transcription Factor” J. Med. Chem., 2013, 56(4), 1739–1747.

39. Babinksi, D.J.; Bao, X.; El Arba, M.; Chen, B.; Hrovat, D.A.; Borden, W.T.; Frantz, D.E. “Synchronized Aromaticity as an Enthalpic Driving Force for the Aromatic Cope Rearrangement” J. Am. Chem. Soc., 2012, 134, 16139.

38. Kato, M.; Han, T.W.; Xie, S.; Shi, K.; Du, X.; Wu, L.C.; Mirzaei, H.; Goldsmith, E.J.; Longggood, J.; Pei, J.; Grishin, N.V.; Frantz, D.E.; Schneider, J.W.; Chen, S.; Li, L.; Sawaya, M.R.; Eisenberg, D.; Tycko, R.; McKnight, S.L. “Cell-free formation of RNA granules: Low complexity sequence domains form dynamic fibers within hydrogels” Cell, 2012, 149, 753-767.

37. Zang, Q.S.; Hesham, S.; Maass, D.L.; Martinez, B.; Ma, L.; Kilgore, J.A.; Williams, N.S.; Frantz, D.E.; Wigginton, J.G.; Nwariaku, F.E.; Wolf, S.E.; Minei, J.P. “Specific Inhibition of mitochondrial oxidative stress suppresses inflammation and improves cardiac function in a rat pneumonia-related sepsis model” American Journal of Physiology-Heart and Circulatory Physiology, 2012, 302, H1847-H1859.

36. Russell, J.L.; Goetsch, S.C.; Aguilar, H.R.; Coe, H.; Luo, X.; Liu, N.; van Rooij, E.; Frantz, D.E.; Schneider, J.W. “Targeting Native Adult Heart Progenitors with Cardiogenic Small Molecules” ACS Chemical Biology, 2012, 7, 1067.

35. Russell, J.L.; Goetsch, S.C.; Aguilar, H.R.; Frantz, D.E.; Schneider, J.W. “Regulated expression of pH sensing G protein-coupled receptor-68 identified through chemical biology defines a new drug target for ischemic heart disease” ACS Chemical Biology, 2012 7, 1077.

34. Hartley, R.M.; Peng, J.; Fest, G.A.; Dakshanamurthy, S.; Frantz, D.E.; Brown, M.L.; Mooberry, S.L. “Polygamain, a new microtubule depolymerizing agent that occupies a unique pharmacophore in the colchicine site” Mol. Pharm., 2012, 81, 431.

33. Mata, M.A.; Satterly, N.; Versteeg, G.A.; Frantz, D.E.; Wei, S.; Williams, N.; Schmolke, M.; Peña-Llopis, S.; Brugarolas, J.; Forst, C.V.; White, M.A.; Garcia-Sastre, A.; Roth, M.G.; Fontoura, B.M.A. “Chemical inhibition of RNA viruses reveals REDD1 as a host defense fact” Nature Chem. Bio., 2011, 7, 712-719.

32. Babinski, D.J.; Aguilar, H.A.; Still, R.; Frantz, D.E. “Synthesis of substituted pyrazoles via tandem cross-coupling/electrocyclization of enol triflates and diazoacetates” J. Org. Chem., 2011, 76, 15, 5915-5923. (Featured Article and Highlighted by Synfacts)

31. Crouch, I.T.; Dreier, T.; Frantz, D.E. “Palladium-catalyzed elimination/isomerization of enol triflates into 1,3-dienes” Angew. Chem. Int. Ed., 2011, 50, 27, 6128-6132. (Highlighted by Synfacts)

30. Wang, Y.X.; Zang, Q.S.; Liu, Z.J.; Wu, Q.; Maass, D.; Dulan, G.; Shaul, P.W.; Melito, L.; Frantz, D.E.; Kilgore, J.A.; Williams, N.S.; Terada, L.S.; Nwariaku, F.E. “Regulation of VEGF-induced endothelial cell migration by mitochondrial reactive oxygen species” Am. J. Phys. Cell Phys., 2011, 301, 3, C695-C704.

29. Zhang, L.; Peng, L.; Hsu, T.; Aguilar, H.R.; Frantz, D.E.; Schneider, J.W.; Bachoo, R.M.; Hsieh, J. “Small-molecule blocks malignant astrocyte proliferation and induces neuronal gene expression” Differentiation, 2011, 81, 4, 233-242.

28. Peng, J.; Jackson, E.M.; Babinski, D.J.; Risinger, A.L.; Helms, G.; Frantz, D.E.; Mooberry, S.L. “Evelynin, a cytotoxic benzoquinone-type retro-dihydrochalcone from Tacca chantrieri” J. Nat. Prod., 2010, 73, 9, 1590-1592.

27. Menzel, K.; Machrouchi, F.; Bodenstein, M.; Alorati, A.; Cowden, C.; Gibson, A.W.; Bishop, B.; Ikemoto, N.; Nelson, T.D.; Kress, M.H.; Frantz, D.E. “Process development of a potent bradykinin 1 antagonist” Org. Process Res. Dev., 2009, 13, 3 , 519–524.

26. Lee, J.; Sperandio, V.; Frantz, D.E.; Longgood, J.; Camilli, A.; Phillips, M.A.; Michael, A.J. “An alternative polyamine biosynthetic pathway is widespread in bacteria and essential for biofilm formation in Vibrio cholerae” J. Biol. Chem., 2009, 284, 15, 9899-907.

25. Schneider, J.W.; Gao, Z.; Li, S.; Farooqi, M.; Tang, T.-S.; Bezprozvanny, I.; Frantz, D.E.; Hsieh, J. “Small-molecule activation of neuronal cell fate” Nature Chem. Bio., 2008, 4, 7, 408.

24. Babinski, D.; Soltani, O.; Frantz, D.E. “Stereoselective synthesis of acetoacetate-derived enol triflates” Org. Lett., 2008, 13 , 2901–2904.

23. Sadek, H.; Hannack, B.; Choe, E.; Wang, J.; Latif, S.; Garry, M.G.; Garry, D.J.; Longgood, J.; Frantz, D.E.; Olson, E.N.; Hsieh, J.; Schneider, J. W. “Cardiogenic small molecules that enhance myocardial repair by stem cells” Proc. Natl. Acad. Sci. U.S.A., 2008, 105, 16, 6063-6068.

22. Menzel, K.; Mills, P.M.; Frantz, D.E.; Nelson, T.D.; Kress, M.H. “Substitution effect on the regioselective halogen/metal exchange of 3-substituted 1,2,5-tribromobenzenes” Tetrahedron Lett., 2008, 49, 415-418.

21. Chen, X.; Longgood, J.C.; Michnoff, C.; Wei, S.; Frantz, D.E.; Bezprozvanny, I. “High-throughput screen for small molecule inhibitors of Mint1-PDZ domains” Assay and Drug Development Technologies, 2007, 5, 769-784.

20. DiMichele, L.; Menzel, K.; Mills, P.; Frantz, D.E.; Nelson, T.D. “Halogen-metal exchange of 3-substituted 1,2-dibromoarenes: The use of long-range J(CH) coupling constants to determine regiochemistry” Magn. Reson. Chem., 2006, 44, 11, 1041-1043.

19. Menzel, K.; Fisher, E.L.; DiMichele, L.; Frantz, D.E.; Nelson, T.D.; Kress, M.H. “An improved method for the bromination of metalated haloarenes via lithium, zinc transmetalation: A convenient synthesis of 1,2-dibromoarenes” J. Org. Chem., 2006, 71, 5, 2188-2191.

18. Menzel, K.; DiMichele, L.; Mills, P.; Frantz, D.E.; Nelson, T.D.; Kress, M.H. “Regioselective halogen-metal exchange reaction of 3-substituted 1,2-dibromo arenes: The synthesis of 2-substituted 5-bromobenzoic acid” Synlett, 2006, 12, 1948-1952.

17. Nelson, T.D.; LeBlond, C.R.; Frantz, D.E.; Matty, L.; Mitten, J.V.; Weaver, D.G.; Moore, J.C.; Kim, J.M.; Boyd, R.; Kim, P.-Y.; Gbewonyo, K.; Brower, M.; Sturr, M.; McLaughlin, K.; McMasters, D.R.; Kress, M.H.; McNamara, J.M.; Dolling, U.H. “Stereoselective synthesis of a potent thrombin inhibitor by a novel P2-P3 lactone ring opening” J. Org. Chem., 2004, 69, 11, 3620-3627.

16. Faessler, R.; Tomooka, C.S.; Frantz, D.E.; Carreira, E.M. “Infrared spectroscopic investigations on the metallation of terminal alkynes by Zn(OTf)2” Proc. Natl. Acad. Sci. U.S.A., 2004, 101, 16, 5843-5845.

15. Frantz, D.E.; Morency, L.; Soheili, A.; Murry, J.A.; Grabowski, E.J.J.; Tillyer, R.D. “Synthesis of substituted imidazoles via organocatalysis” Org. Lett., 2004, 6, 5, 843-846.

14. Frantz, D.E.; Weaver, D.G.; Carey, J.P.; Kress, M.H.; Dolling, U.H. “Practical synthesis of aryl triflates under aqueous conditions” Org. Lett., 2002, 4, 26, 4717-4718.

13. Fassler, R.; Frantz, D.E.; Oetiker, J.; Carreira, E.M. “First synthesis of optically pure propargylic N-hydroxylamines by direct, highly diastereoselective addition of terminal alkynes to nitrones” Angew. Chem. Int. Ed., 2002, 41, 16, 3054-3056.

12. Boyall, D.; Frantz, D.E.; Carreira, E.M. “Efficient enantioselective additions of terminal alkynes and aldehydes under operationally convenient conditions” Org. Lett., 2002, 4, 15, 2605-2606.

11. Frey, L.F.; Marcantonio, K.; Frantz, D.E.; Murry, J.A.; Tillyer, R.D.; Grabowski, E.J.J.; Reider, P.J. “Practical routes toward the synthesis of 2-halo and 2-alkylamine-4-pyridinecarboxaldehydes” Tetrahedron Lett., 2001, 42, 39, 6815-6818.

10. Murry, J.A.; Frantz, D.E.; Soheili, A.; Tillyer, R.D.; Grabowski, E.J.J.; Reider, P.J. “Synthesis of alpha-amido ketones via organic catalysis: Thiazolium-catalyzed cross-coupling of aldehydes with acylimines” J. Am. Chem. Soc., 2001, 123, 39, 9696-9697.

9. Frantz, D.E.; Fassler, R.; Tomooka, C.S.; Carreira, E.M. “The discovery of novel reactivity in the development of C-C bond-forming reactions: In situ generation of zinc acetylides with Zn(II)/R3N” Acc. Chem. Res., 2000; 33, 6, 373-38.

8. Aschwanden, P.; Frantz, D.E.; Carreira, E.M. “Synthesis of 2,3-dihydroisoxazoles from propargylic N-hydroxylamines via Zn(II)-catalyzed ring-closure reaction” Org. Lett., 2000, 2, 15, 2331-2333.

7. Frantz, D.E.; Singleton, D.A. “Isotope effects and the mechanism of chlorotrimethylsilane-mediated addition of cuprates to enones” J. Am. Chem. Soc., 2000, 122, 14, 3288-3295.

6. Boyall, D.; Lopez, H.; Sasaki, H.; Frantz, D.E.; Carreira, E.M. “Enantioselective addition of 2-methyl-3-butyn-2-ol to aldehydes: Preparation of 3-hydroxy-1-butynes” Org. Lett., 2000, 2, 26 , 4233–4236.

5. Frantz, D.E.; Faessler, R.; Carreira, E.M. “Facile enantioselective synthesis of propargyl alcohols by direct, highly diastereoselective addition of terminal alkynes to aldehdyes” J. Am. Chem. Soc., 2000, 122, 8, 1806-1807.

4. Frantz, D.E.; Faessler, R.; Carreira, E.M. “Catalytic in situ generation of Zn(II)-alkynilides under mild conditions: A novel C=N addition process utilizing terminal acetylenes” J. Am. Chem. Soc., 1999, 121, 48, 11245-11246.

3. Frantz, D.E.; Singleton, D.A. “Carbometalations of simple alkenes with allyldibromoborane” Org. Lett., 1999, 1, 485-486.

2. Frantz, D.E.; Singleton, D.A.; Snyder, J.P. " 13C kinetic isotope effects for the addition of lithium dibutylcuprate to cyclohexenone. Reductive elimination is rate-determining" J. Am. Chem. Soc., 1997, 119, 3383-3384.

1. Singleton, D.A.; Waller, S.C.; Zhang, Z.; Frantz, D.E.; Leung, S.-W. “Allylboration of alkenes with allyldihaloboranes” J. Am. Chem. Soc., 1996, 118, 9986-9987.

Publications | The Frantz Lab

Full Publications List