Department of Chemistry

Search

FourSquare

Kay M. Brummond

Professor and Associate Dean for Faculty

Contact

807 CHVRN
Chevron Science Center
219 Parkman Avenue

Pittsburgh, PA 15260
412-624-1955

My Website >

Research Overview

Organic Chemistry, Transition-Metal Catalysis, Cycloadditions, Natural Product Synthesis

Targeted Covalent Inhibitors. Our team designs and synthesizes guaianolide analogs with muted thiol reactivity to gain access to meaningful SAR data for this class of bioactive compounds. Our approach uses an allylboration/cyclization process and an allenic Pauson–Khand reaction (APKR) to rapidly assemble the 5,7,5-ring system. Additionally, we exchange the highly reactive α-methylene–γ-lactone with an α-methylene–γ-lactam–a covalent reactive group with thiol reactivity that can be regulated in predictable ways. We are testing our hypothesis in the rational design of covalent inhibitors with low reactivity and high affinity for the kinase and protease enzyme targets, VASH1 and SARS-CoV-2 main protease.

Transition-Metal Catalysis. Our team designs and synthesizes transition-metal catalysts to control reaction outcomes such as product selectivity and yield. Our approach uses a deep mechanistic understanding informed by a real-time collaboration between experimental and computational organic chemists. In this way, we have synthesized 5,7-ring systems with high enantioselectivity enabled through a stereoconvergent Rh(I)-catalyzed allenic Pauson–Khand reaction. We are applying these findings to the enantioselective synthesis of thapsigargin and we are extending this mechanistic approach to other systems including the PKR of enynes.

Dearomative Cycloaddition Reactions. Our team identifies factors that govern reactivity and product selectivity in the dearomative didehydro-Diels–Alder (DDDA) reaction of heteroarenes. Our approach uses an iterative, real-time collaboration between experimental and computational organic chemists to gain mechanistic insight. We expect that revealing the key reactivity factors will inform other cyclization and cycloaddition reactions involving de-aromatization and re-aromatization processes. Additionally, we are applying these findings to the synthesis of novel ladder-type heteroarene compounds for use in high performing organic photovoltaic materials.

Complete Listing of Published Work in MyBibliography:

http://www.ncbi.nlm.nih.gov/myncbi/browse/collection/50348838/?sort=date...

Awards

  • 2021 American Chemical Society Award for Encouraging Women into Careers in the Chemical Sciences sponsored by the Camille and Henry Dreyfus Foundation
  • 2020 Featured as Remarkable Woman in Organic Chemistry in ACS Symposium, see: https://www.organicdivision.org/blog/2020/04/29/virtual-symposium-april-29-2020/
  • 2019 Plenary Speaker at the National Organic Chemistry Symposium, see: https://www.organicdivision.org/nos-2019-lecture-videos/
  • 2018 Chancellor's Distinguished Public Service Award
  • 2018 Selected for Atlantic Coast Conference Academic Leaders Network Program
  • 2018 Provost's Spotlight on Women Leaders Series (https://www.youtube.com/watch?v=IUWCJeN3xwM&feature=youtu.be)
  • 2017 Executive Director of the 45th National Organic Symposium
  • 2016 Harold Kohn Endowed Alumni Lectureship awarded by Penn State University
  • 2016 Oxide Diversity Catalyst Lecture
  • 2015 ACS Pittsburgh Award
  • 2011 Visiting Fellow, University of New South Wales, Sydney, Australia
  • 2010 Visiting Professor, Université Pierre et Marie Curie-Paris 6, Paris, France
  • 2008 Visiting Professor, Department of Chemistry, MIT, Boston, MA
  • 2007 Carnegie Science Center Award-Emerging Female Scientist
  • 2007 American Chemical Society Akron Section Award
  • 2006–2008 Alternate Councilor, Division of Organic Chemistry-ACS, Elected
  • 2005–2009 NIH Synthetic and Biological Chemistry Study Section A, Permanent Member
  • 2006–2014 Board of Editors, Organic Syntheses
  • 2010 American Chemical Society Fellow
  • 2003 Chancellor’s Distinguished Research Award, Junior Scholar Awardee
  • 2002 Johnson & Johnson Focused Giving Award
  • 1999 Departmental Outstanding Faculty Award, Department of Chemistry, WVU
  • 1998 National Science Foundation-CAREER Award, (declined to accept NIH Award)

Publications

“Origins of Enantioselectivity in the Rh(I)-catalyzed Pauson–Khand Reaction: Comparison of Bidentate and Monodentate Chiral Ligands,” Lauren C. Burrows, Luke T. Jesikowicz, Peng Liu* and Kay M. Brummond* ACS Catalysis 2021, 11, 323-336
“Synthesis of Guaianolide Analogues with a Tunable α-Methylene–γ-Lactam Electrophile and Correlating Bioactivity with Thiol Reactivity,” Paul A. Jackson, Henry A. M. Schares, Katherine F.M. Jones, John C. Widen, Daniel P. Dempe, Matthew E. Cuellar, Michael A. Walters, Daniel A. Harki* and Kay M. Brummond* J. Med. Chem 2020, 63, 14951-14978
“Computationally Guided Catalyst Design in the Type I Dynamic Kinetic Asymmetric Pauson–Khand Reaction of Allenyl Acetates,” Lauren Parrette, Luke Jesikiewicz, Gang Lu, Steve Geib, Peng Liu,* Kay Brummond* J. Am. Chem. Soc. 2017, 139, 15022-15032.
“Covalent Modifiers: A Chemical Perspective on the Reactivity of α,β-Unsaturated Carbonyls with Thiols via Hetero-Michael Addition Reactions,” Paul A. Jackson,† John C. Widen,‡ Daniel A. Harki,‡,*, and Kay M. Brummond,†* J. Med. Chem. 2017, 60, 839-885.
“Intramolecular Didehydro-Diels–Alder Reaction for the Synthesis of Benzo- and Dihydrobenzo-Fused Heterocycles,” Ashley Bober, Justin T. Proto, and Kay M. Brummond*. Org. Lett. 2017, 19, 1500-1503.
“Rhodium(I)-catalyzed Allenic Pauson-Khand Reaction,” Joseph E. Burchick. Jr., Sarah M. Wells, and Kay M. Brummond* Organic Syntheses. 2017, 94, 109.
“Alkyne Ligation Handles: Propargylation of Hydroxyl, Sulfhydryl, Amino and Carboxyl Groups via the Nicholas Reaction,” Sarah M. Wells,† John C. Widen,‡ Daniel A. Harki,‡* and Kay M. Brummond,†* Org. Lett. 2016, 18, 4566-4569.
“An Intramolecular Dehydro-Diels–Alder Reaction and Its Impact on the Structure-Function Properties of Environmentally Sensitive Fluorophores,” Kay M. Brummond* and Laura S. Kocsis Acc. Chem. Res. Special Thematic Issue on Synthesis Design and Molecular Function. 2015, 48, 2320–2329.
“Mechanistic Insight into the Dehydro-Diels-Alder Reaction of Styrene-ynes,” Laura S. Kocsis, Husain N. Kagalwala, Sharlene Mutto, Bhaskar Godugu, Stefan Bernhard, Dean J. Tantillo, and Kay M. Brummond* J. Org. Chem. JOC special issue entitled “50 Years and Counting: The Woodward–Hoffman Rules in the 21st Century.” 2015, 80, 2965-2973.
“Cyclopenta[b]naphthalene Cyanoacrylate Dyes: Synthesis and Evaluation as Fluorescent Molecular Rotors,” Laura S. Kocsis, Kristyna M. Elbel, Billie A. Hardigree, Kay M. Brummond*, Mark A. Haidekker and Emmanuel A. Theodorakis Org. & Biomol. Chem. Paper from themed collection 2015 Hot Articles in Organic and Biomolecular Chemistry 2015, 13, 2965-2973.
“Organic Syntheses,” Kay M. Brummond (editor) Volume 91 2015, Wiley
“Functionalized Naphthalene Fluorophores,”  Kay M. Brummond, Laura S. Kocsis, and Erica Benedetti U.S. Patent No. 9 133 234 B2 Issued September 15 2015
“Synthesis, Structure and Use of Functionalized Naphthalenes,” Kay M. Brummond, Laura S. Kocsis, and Erica Benedetti U.S. Patent No. 9 102 703 B2 Issued August 11 2015
“Synthesis, Structure and Use of Functionalized Naphthalenes,” Kay M. Brummond, Laura S. Kocsis, and Erica Benedetti U.S. Patent Application Serial No. 14/822 858 Filed August 10 2015
“Identification of ATR-Chk1 Pathway Inhibitors that Selectively Target p53-Deficient Cells Without Directly Suppressing ATR Catalytic Activity,” Masaoki Kawasumi, James E. Bradner, Nicola Tolliday, Renee Thibodeau, Heather Sloan, Kay M. Brummond and Paul Nghiem Cancer Research 2014, 74, 7534-7545.
“A Redox Economical Synthesis of Bioactive 6,12-Guaianolides,” Bo Wen, Joseph K. Hexum, John C. Widen, Daniel A. Harki and Kay M. Brummond* Org. Lett. 2013, 15, 2644-1647.
“Synthesis and Photophysical Properties of a Series of Cyclopenta[b]naphthalene Solvatochromic Fluorophores,” Erica Benedetti, Laura S. Kocsis and Kay M. Brummond* J. Am. Chem. Soc. 2012, 134, 11418-12421.
“A Thermal Dehydrogenative Diels–Alder Reaction of Styrenes for the Concise Synthesis of Functionalized Naphthalenes,” Laura S. Kocsis, Erica Benedetti and Kay M. Brummond* Org. Lett. 2012, 14, 4430-4433.
“Chemical Methodology as a Source of Small-Molecule Checkpoint Inhibitors and Hsp70 Modulators.,” Donna M. Huryn, Jeffrey L. Brodsky, Kay M. Brummond, Peter G. Chambers, Benjamin Eyre, Alex W. Ireland, Masaoki Kawasumi, Matthew G. LaPorte, Kayla Lloyd, Baptiste Manteau, Paul Nghiem, Bettina Quade, Sandlin P. Seguin, and Peter Wipf Proceedings of the National Academy of Sciences of the United States of America. 2011, 108, 6757-6762.
“Differentiating Mechanistic Possibilities for the Thermal, Intramolecular [2+2] Cycloaddition of Allene-Ynes,” Siebert MR, Osbourn JM, Brummond* KM, et al. Journal of the American Chemical Society 2010, 132, 11952-11966.