个人简介
POSITIONS AND EDUCATION
University of Chicago Assistant Professor (2019 – 2022)
Associate Professor (2022 – Present)
Harvard University NIH Postdoctoral Fellow (2017-2019)
Advisor: Eric N. Jacobsen
University of California, Berkeley Ph.D. in Chemistry (2012-2017)
NSF Graduate Research Fellow
ARCS Graduate Research Fellow
Advisor: F. Dean Toste
University of Rochester B.S. in Chemistry (2008-2012)
Advisor: Alison J. Frontier
NARRATIVE BIOSKETCH
Mark was born and raised in Cleveland, OH as the oldest of three children in a Russian-Jewish immigrant family. In 2012, he earned a B.S. in chemistry from the University of Rochester in Rochester, NY, conducting undergraduate research with Professor Alison J. Frontier on an oxidative variant of the Nazarov cyclization. Through participation in the DAAD RISE program, Mark also spent the summer of 2010 conducting research with Henning Hopf at TU Braunschweig on the synthesis of strained hydrocarbons. After graduation, he joined the laboratory of Professor F. Dean Toste at the University of California, Berkeley. There, he studied the chemistry of the Au(I)/Au(III) redox couple in several contexts, including supramolecular catalysis and fluorine-18 radiosynthesis. After earning his Ph.D. in 2017, Mark joined the laboratory of Professor Eric N. Jacobsen as an NIH Postdoctoral Fellow at Harvard University where his research focused on enantioselective fluorination reactions with chiral organoiodane catalysts. In 2019, Mark joined the University of Chicago as an assistant professor of chemistry and was promoted to associate professor with tenure in 2022. His research interests include the development of synthetic methodology and study of their mechanisms, with a specific focus on “single-atom skeletal editing”.
AWARDS
Arthur C. Cope Scholar Award, 2023
Bristol Myers Squibb Unrestricted Research Grant, 2023
NSF CAREER, 2023
Bayer Early Excellence in Science Award, 2023
Amgen Young Investigator Award, 2022
FMC New Investigator Award, 2022
Camille Dreyfus Teacher-Scholar Award, 2022
Sloan Foundation Fellowship, 2022
Thieme Chemistry Journal Award, 2022
David and Lucille Packard Foundation Fellowship, 2021
Cancer Research Foundation Young Investigator Award, 2020
Reaxys Ph.D. Prize Finalist, 2017
Andrew Dorsey Memorial Award for Excellence in Teaching, 2015
Dr. E.W. and Maude V. Flagg Award, 2012
Carl A. Whiteman Teaching Award, 2012
Phi Beta Kappa, University of Rochester, 2011
Barry M. Goldwater Honorable Mention, 2010
Merck Index Award, 2010
Iota Book Award, 2010
研究领域
“EXOTIC” SPECIES AS INSPIRATION
The reach of synthetic chemistry has provided information on a wide range of structurally unusual species, many of which show otherwise unprecedented patterns of reactivity. Harnessing such precedents for the development of synthetically useful transformations which expand the complement of available retrosynthetic disconnections is a key focus of our laboratory. Such research naturally bridges organic, inorganic, and organometallic synthesis, with lessons from mechanistic elucidation serving subsequently as a design tool.
SINGLE-ATOM SKELETAL EDITING
Although modern organic synthesis allows for the preparation of most envisioned target structures, such endeavors still often require lengthy campaigns, and the preparation of related species can often necessitate re-engineering of the synthetic route altogether. This is in contrast to the philosophical approach of lead-optimization central to medicinal chemistry, wherein structure-activity relationships are established via changes to a parent scaffold. Though much progress has been made in C-H functionalization approaches towards this goal, we seek to bring synthetic methodologies to bear which enable the direct interrogation of single-atom insertions and deletions of the constitutive elements of ring and chain systems.
METHODS FOR ISOTOPE LABELING AND RADIOSYNTHESIS
A natural outgrowth of our focus on single-atom editing is the ability to instal isotopic labels into traditionally challenging sites of the molecule. In addition to stable and long-lived isotopes (e.g. carbon-13 or carbon-14), methods for the synthesis of short-lived positron emitting isotopes with relevance to PET imaging are being developed in partnership with the Cyclotron Facility at the University of Chicago.
近期论文
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Carbon-to-nitrogen single-atom transmutation of azaarenes Woo, J.; Stein, C.; Christian, A.H.; Levin, M.D.Nature, 2023, 623, 77–82.
Evidence for Dearomatizing Spirocyclization and Dynamic Effects in the Nitrogen Deletion of Tetrahydroisoquinolines Masson-Makdissi, J.; Lalisse, R.F.; Yuan, M.; Dherange, B.D.; Gutierrez, O.; Levin, M.D.
Aromatic Nitrogen Scanning by Ipso-Selective Nitrene Internalization Pearson, T.J.; Shimazumi, R.; Driscoll, J.L.; Dherange, B.D.; Park, D.; Levin, M.D. Science 2023, 381(6665), 1474-1479.
A Focus on 1-Azahomocubane: the New Kid on the Block Elgindy, C.; Levin, M.D. Chem. Sci. 2023, 14, 7608 – 7610
Core-Labeling (Radio)Synthesis of Phenols Lynch, C.F.; Downey,J.W.; Zhang, Y.; Hooker, J.M.; Levin, M.D. Org. Lett. 2023, ASAP.
N-(Benzyloxy)-N-(pivaloyloxy)-4-(trifluoromethyl)-benzamide Berger, K.J.; Dherange, B.D.; Morales, M.; Driscoll, J.L. Tarhan, A.K.; Levin, M.D. Org. Syn. 2023, 100, 113-135.
Direct Deaminative Functionalization Dherange,B.D.; Yuan,M.; Kelly, C.B.; Reiher, C.A.; Grosanu, C.; Berger,K.J.; Gutierrez, O.; Levin, M.D. J. Am. Chem. Soc. 2023, 145(1), 17-24.
C−C Coupling through Nitrogen Deletion: Application to Library Synthesis Holovach,S.; Melnykov, K.P.; Poroshyn, I.; Iminov, R.T.; Dudenko, D. Kondratov, I.; Levin, M.D.; Grygorenko, O.O. Chem. Eur. J. 2023, 29(4), e202203470.
Unified Access to Pyrimidines and Quinazolines Enabled by N-N Cleaving Carbon Atom Insertion Hyland, E.E.; Kelly, P.Q.; McKillop, A.M.; Dherange, B.D.; Levin, M.D. J. Am. Chem. Soc. 2022, 144(42), 19258–19264
A Synthetic Cycle for Heteroarene Synthesis by Nitride Insertion Kelly, P.Q.; Filatov, A.S.; Levin, M.D.Angew. Chem. Int. Ed. 2022, 61(46), e202213041.
Scaffold Hopping by Net Photochemical Carbon Deletion of Azaarenes Woo, J.; Christian, A.H.; Burgess, S.A.; Jiang, Y.; Mansoor, U.F.; Levin, M.D. Science, 2022, 376(6593), 527-532.
Single-Atom Logic for Heterocycle Editing Jurczyk, J.; Woo, J.; Kim, S.F.; Dherange, B.D.; Sarpong, R.; Levin, M.D. Nat. Synth. 2022,1, 352-364.
Direct Deamination of Primary Amines via Isodiazene Intermediates Berger, K.J.; Driscoll, J.L.; Yuan, M.; Dherange, B.D.; Gutierrez, O.; Levin, M.D. J. Am. Chem. Soc. 2021, 143(42), 17366–17373.
Carbon Atom Insertion into Pyrroles and Indoles Promoted by Chlorodiazirines Dherange, B.D.; Kelly, P.Q.; Liles, J.P.; Sigman, M.S.; Levin, M.D. J. Am. Chem. Soc. 2021, 143(30), 11337-11344
Skeletal Editing Through Direct Nitrogen Deletion of Secondary Amines Kennedy, S.H.; Dherange, B.D.; Berger, K.J. Levin, M.D. Nature, 2021, 593, 223–227.
Reframing Primary Alkyl Amines as Aliphatic Building Blocks Berger, K.J; Levin, M.D. Org. Biomol. Chem. 2021, 19, 11-36.
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