Professor, Organic Chemistry
office: CSL 208
- B.S., Chemistry; San Diego State University, 2006
- Ph.D., Organic Chemistry; Yale University, 2011
- NIH Postdoctoral Fellow; Yale University, 2011-2013
Research in the Gustafson group strives to apply innovative chemical strategies towards complex biological problems. Ongoing projects focus on three main areas (a) The development of chemical methodologies that enable the enantioselective synthesis of complex molecules; (b) The application of these methodologies to access new selective small molecule probes pertaining to aberrant protein phosphorylation; and (c) The design, synthesis and evaluation of small molecule vanadate complexes as phosphatase inhibitors.
Graduate students who join my lab will receive a thorough training in organic chemistry (i.e. asymmetric catalysis, organic synthesis, medicinal chemistry). Cutting edge analytical techniques such as NMR spectroscopy and HPLC will be constantly utilized to analyze each reaction. Additionally, the interdisciplinary nature of this research will expose graduate students to diverse techniques from other disciplines such as molecular biology (recombinant protein synthesis and purification, Western blot analysis) and biochemistry (in vitro inhibition assays). As time progresses gifted students will be able to emphasize any or all of these areas depending on their interests. As a new faculty member I am actively recruiting talented Masters and Ph.D. students to join my lab.
As an alumnus of SDSU who has greatly benefitted from participating in undergraduate research, I understand the vital importance of these endeavors towards the career advancement of SDSU students, and thus enthusiastically encourage talented undergraduates to perform research in my laboratory.
Selected publications at SDSU :(in reverse chronological order)
- "Redox-Responsive H-Bonding: Amplifying the Effect of Electron Transfer Using Proton-Coupled Electron Transfer,"
Hyejeong Choi, Kiyeol Baek, Sean T. Toenjes, Jeffrey L. Gustafson, and Diane Kimball Smith,
J. Am. Chem. Soc. in press (2020). (doi: 10.1021/jacs.0c07841.)
- "Discovery of cyclic guanidine-linked sulfonamides as inhibitors of LMTK3 kinase,"
Maria A. Ortiz, Heather Michaels, Brandon Molina, Sean Toenjes, Jennifer Davis, Guya Diletta Marconi, David Hecht, Jeffrey L. Gustafson, F. Javier Piedrafita, Adel Nefzi,
Biol. & Medicinal Chem. Lett. 30, 127108 (2020). (10.1016/j.bmcl.2020.127108.)
- "Catalytic Atroposelective Synthesis of N-Aryl Quinoid Compounds,"
Sagar Dilip Vaidya, Sean T. Toenjes, Nobuyuki Yamamoto, Sean M Maddox, and Jeffrey L. Gustafson,
J. Am. Chem. Soc. 142, 2198-2203 (2020). (doi: 10.1021/jacs.9b1299.)
- "Photocatalytic Oxidative C—H Thiolation: Synthesis of Benzothiazoles and Sulfenylated Indoles,"
Andrew N. Dinh, Ashley D. Nguyen, Ernesto Millan Aceves, Samuel T. Albright, Mario R. Cedano, Diane K. Smith, Jeffrey L. Gustafson,
Synlett 30, 1648-1655 (2019). (doi: 10.1055/s-0039-1690107.)
- "Leveraging Atropisomerism to Obtain a Selective Inhibitor of RET Kinase with Secondary Activities toward EGFR Mutants,"
Sean T. Toenjes, Valeria Garcia, Sean M. Maddox, Gregory A. Dawson, Maria A. Ortiz, F. Javier Piedrafita, Jeffrey L. Gustafson,
ACS Chem. Biol. 14, 1930-1939 (2019). (doi: 10.1021/acschembio.9b00407.)
- "Toward a Catalytic Atroposelective Synthesis of Diaryl Ethers Through C(sp (2) )-H Alkylation with Nitroalkanes,"
Dinh, Andrew N.; Noorbehesht, Ryan R.; Toenjes, Sean T., Amy C. Jackson, Mirza A. Saputra, Sean M. Maddox, Jeffrey L. Gustafson,
Synlett 29, 2155-2160 (2018). (: 10.1055/s-0037-1609581.)
- "Enantioselective Synthesis of Biaryl Atropisomers via the Addition of Thiophenols into Aryl-Naphthoquinones,"
Sean M. Maddox, Gregory A. Dawson, Nicholas C. Rochester, Arianna B. Ayonon, Curtis E. Moore, Arnold L. Rheingold, Jeffrey L. Gustafson,
ACS Catal. 86, 5443-5447 (2018). (doi: 10.1021/acscatal.8b00906.)
- "Lewis Base/Bronsted Acid Dual-Catalytic C–H Sulfenylation of Aromatics,"
Christopher J. Nalbandian, Zachary E. Brown, Erik Alvarez, and Jeffrey L. Gustafson,
Org. Lett. 2011, 3211-3214 (2018). (doi: acs.orglett.8b01066.)
- "Enantioselective Synthesis of Pyrrolopyrimidine Scaffolds through Cation-Directed Nucleophilic Aromatic Substitution,"
Mariel M. Cardenas, Sean T. Toenjes, Christopher J. Nalbandian, Jeffrey L. Gustafson,
Org. Lett. 207, 2037-2041 (2018). (doi: 10.1021/acs.orglett.8b00579.)
- "Atropisomerism in medicinal chemistry: challenges and opportunities,"
Sean T. Toenjes and Jeffrey L. Gustafson,
Future Med. Chem. 10, 409-422 (2018). (doi: 10.4155/fmc-2017-0152.)
- "Benzylic bromination catalyzed by triphenylphosphine selenide via Lewis basic activation,"
Arianna Ayonon, Christopher Nalbandian, Lucas Guillemard, Jeffrey Gustafson,
Tetrahedron Lett. 58, 2940-2943 (2017). (doi: 10.1016/j.tetlet.2017.06.042.)
- "A conjugate Lewis base-Bronsted acid catalyst for the sulfenylation of nitrogen containing heterocycles under mild conditions,"
Nalbandian, C.; Miller, E.; Toenjes, S.; Gustafson, J. L.,
Chem. Commun. 53, 1494-1497 (2017). (doi: 10.1039/C6CC09998J.)
- "The Catalyst Controlled Regiodivergent Chlorination of Phenols,"
Maddox, S. M.; Dinh, A,N.; Armenta, F.; Um, J.; Gustafson, J.,
Org. Lett. 18, 5476-5479 (2016). (doi: 10.1021/acs.orglett.6b0265.)
Selected publications before SDSU:
- Dynamic Kinetic Resolution of Biaryl Atropisomers via Peptide-Catalyzed Bromination. Gustafson, J. L.; Lim, D.; Miller, S. J. Science 2010, 328, 1251-1255.
- Synthesis of Atropisomerically Defined, Highly Substituted Biaryl Scaffolds through Catalytic Enantioselective Bromination and Regioselective Cross-Coupling. Gustafson, J. L.; Lim, D.; Barrett, K.; Miller, S. J. Angew. Chem. Int. Ed. 2011, 50, 5025-5029.
- Linear Free Energy Relationship Analysis of a Catalytic Desymmetrization of Diarylmethane-Bis(phenol). Gustafson, J. L.; Sigman, M. S.; Miller, S. J. Org. Lett. 2010. 12, 2794-2797.
- Small Molecule Inhibitors of the Interaction Between the E3 Ligase VHL and HIF1α Buckley, D. L.; Gustafson, J. L.; Van Molle, I.; Roth, A. G.; Tae, H.S.; Gareiss, P.C.; Jorgensen, W. L.; Ciulli, A.; Crews, C. M. Angew. Chem. Int. Ed. 2012, 51, 11463-11467.
- Extensive Isomerization of Alkenes using a Bifunctional Catalyst: An Alkene Zipper. Grotjahn, D. B.; Larsen, C. R.; Gustafson, J. L.; Nair, R.; Sharma, A. J. Am. Chem. Soc. 2007, 129, 9592-9593.