Thiol Reactivity of N-Aryl α-Methylene-γ-Lactams: A Reactive Group for Targeted Covalent Inhibitor Design

Tuğçe G. Erbay, Daniel P. Dempe, Bhaskar Godugu, Peng Liu,* Kay M. Brummond.* Submitted to JOC.

Mechanism and Origins of Enantioselectivity in the Rh(I)-catalyzed Pauson–Khand Reaction: Comparison of Bidentate and Monodentate Chiral Ligands

Lauren C. Burrows,† Luke T. Jesikiewicz,† Peng Liu,*,†,‡ and Kay M. Brummond*,† ACS Catal. 2021, 11, 1, 323-336.

Synthesis of Guaianolide Analogs with a Tunable α-Methylene-γ-Lactam Electrophile and Correlating Bioactivity with Thiol Reactivity

Paul A. Jackson, Henry A. M. Schares, Katherine F. Jones, John C. Widen, Daniel Dempe, Matthew Cuellar, Michael Walters, Daniel A. Harki* and Kay M. Brummond.* J. Med. Chem. 2020, 63, 23, 14951-14978.

Lauren Parrette, Luke Jesikiewicz, Gang Lu, Steve Geib, Peng Liu,* Kay Brummond,* J. Am. Chem. Soc2017139, 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. Chem201760, 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. Res2015Acc. Chem. Res., 2015, 48, 2320–2329. Special Issue on Synthesis, Design and Molecular Function.

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. Chem201580, 13, 2965-2973. JOC special issue entitled “50 Years and Counting: The Woodward–Hoffman Rules in the 21st Century.”

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. Chem2015, 13, 2965-2973. 

Conditions for a Rh(I)-Catalyzed [2 + 2 + 1] Cycloaddition Reaction with Methyl Substituted Allenes and Alkynes

Sarah M. Wells and Kay M. Brummond, Tetrahedron Lett2015, 56, 3546-59.

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 Research201474, 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. Lett201315, 2644-2647.

Attachable Solvatochromic Fluorophores and Bioconjugation Studies

Erica Benedetti, Andrea B.E. Veliz, Mélanie Charpenay, Laura Kocsis, and Kay M. Brummond, Org. Lett201315, 2578-2581.

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. Soc2012134, 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. Lett201214, 4430-4433.

Synthesis and in Silico Screening of a Library of β-Carboline-Containing Compounds

Kay M. Brummond, John R. Goodell, Matthew G. LaPorte, Lirong Wang, and Xiang-Qun Xie, Beilstein J. Org. Chem20128, 1048-1058.

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 (PNAS).  2011108, 6757-6762.

Diverging DOS Strategy Using an Allene-Containing Tryptophan Scaffold and a Library Design that Maximizes Biologically Relevant Chemical Space While Minimizing the Number of Compounds

Thomas O. Painter, Lirong Wang, Supriyo Majumder, Xiang-Qun Xie, and Kay M. Brummond, ACS Comb. Sci. 2011, 13, 166-174.

An Allenic Pauson-Khand Approach to 6,12-Guaianolides

Francois Grillet, Chaofeng Huang, and Kay M. Brummond, Org. Lett201113, 6304-6307.

Allenes: The Changing Landscape of Csp

Kay M. Brummond, Beilstein J. Org. Chem20117, 394-395.

Differentiating Mechanistic Possibilities for the Thermal Intramolecular [2 + 2] Cycloaddition of Allene-ynes

Matthew Siebert, Joshua M. Osbourn, Kay M. Brummond, and Dean J. Tantillo, J. Am. Chem. Soc2010132, 11952-11966.

A Thermally-Induced, Tandem [3,3]-Sigmatropic Rearrangement/[2 +2] Cycloaddition Approach to Carbocyclic Spirooxindoles

Kay M. Brummond and Joshua M. Osbourn, Beilstein J. Org. Chem20106, No. 33.

Rh(I)-Catalyzed Cyclocarbonylation of Allenol Esters to Prepare Acetoxy 4-Alkylidene Cyclopent-3-en-2-ones

Kay M. Brummond and Matthew Davis, J. Org. Chem200974, 8314-8320.

Cdc25B Dual Specificity Phosphatase Inhibitors Identified in a High Throughput Screen of the NIH Compound Library

Paul A. Johnston, Caleb Foster, Marni Brisson Tierno, Tong Ying Shun, Sunita N. Shinde, William D. Paquette, Kay M. Brummond, Peter Wipf, and John S. Lazo, Assay and Drug Development Technologies 2009, 7, 253-265.

Design and Synthesis of a Library of Tetracyclic Hydroazulenoisoindole

Kay M. Brummond, Shuli, Mao, Sunita N. Shinde, Paul A. Johnston, and Billy W. Day, J. Comb. Chem. 2009, 10, 486-494.

Skeletal and Appendage Diversity as Design Elements in the Synthesis of a Discovery Library of Nonaromatic Polycyclic 5-Iminooxazolidin-2-ones, Hydantoins, and Acylureas

Stefan Werner, David M. Turner, Pete G. Chambers, and Kay M. Brummond, Tetrahedron Symposia-in-Print, Synthetic Advances in Transition Metal-Catalyzed Bond-Forming Reactions 2008, 64, 6997-7007.

A General Synthetic Route to Differentially Functionalized Angularly and Linearly Fused [6-7-5] Ring Systems: A Rh(I)-Catalyzed Cyclocarbonylation Reaction

Kay M. Brummond, Daitao Chen, and Matthew M. Davis, J. Org. Chem200873, 5064-5068.

Towards a Molecular Understanding of the Interaction of Dual-Specificity Phosphates with Substrates: Insights from Structure-Based Modeling and High Throughput Screening

Ahmet Bakan, John S. Lazo, Peter Wipf, Kay M. Brummond, and Ivet Bahar, Current Medicinal Chemistry 200815, 2536-2544. 

Diverging Rh(I)-Catalyzed Carbocyclization Strategy to Prepare a Library of Unique Cyclic Ethers

Shuli Mao, Donald A. Probst, Stefan Werner, Jianzhong Chen, Xiangqun Xie, and Kay M. Brummond, J. Comb. Chem. 2008, 10, 235-246.

A Rh(I)-Catalyzed Cycloisomerization Reaction Affording Cyclic Trienones

Kay M. Brummond, Daitao Chen, Thomas O. Painter, Shuli Mao and Darla D. Seifried Synlett 2008, 759-764. Cluster: Acetylene and Allene Chemistry.

Rhodium(I)-Catalyzed Allenic Carbocyclization Reaction Affording δ- and ε-Lactams

Kay M. Brummond, Thomas O. Painter, Donald A. Probst, and Branko Mitasev, Org. Lett. 2007, 9, 347-349.

Structurally Unique Inhibitors of Human Mitogen-activated Protein Kinase Phosphatase-1 Identified in a Pyrrole Carboxamide Library

John S. Lazo, John J. Skoko, Stefan Werner, Branko Mitasev, Ahmet Bakan, Fumito Koizumi, Archibong Yellow-Duke, Ivet Bahar, and Kay M. Brummond, J. Pharmacol. & Experimental Therapeutics 2007, 322, 940-947.

Design and Synthesis of a 3,4-Dehydroproline Amide Discovery Library

Stefan Werner, Dhanalakshmi Kasi, and Kay M. Brummond, J. Comb. Chem. 2007, 9, 677-683.

Cycloaddition Reactions of Amino-Acid Derived Cross-Conjugated Trienes: Stereoselective Synthesis of Novel Heterocyclic Scaffolds

Branko Mitasev, Bingli Yan, and Kay M. Brummond, Heterocycles2006,70, 367-388. Honorary Issue for Professor Steven Weinreb.

The Allenic Alder-ene Reaction: Constitutional Group Selectivity and its Application to the Synthesis of Ovalicin

Kay M. Brummond and Jamie M. McCabe, Tetrahedron Symposia-in-Print, New Applications of Metal Catalysis in Natural Product Synthesis 2006, 62, 10541-10554.

Synthesis of Functionalized ∆3-Pyrrolines via a Ag(I)-Catalyzed Cyclization of Amino Acid Derived Allenes

Branko Mitasev and Kay M. Brummond, Synlett 2006, 3100-3104. Honorary Issue for Professor Richard Heck.

Solution-Phase Synthesis of a Tricyclic Pyrrole-2-Carboxamide Discovery Library Applying a Stetter-Paal-Knorr Reaction Sequence

Stefan Werner, Pravin S. Iyer, Matthew D. Fodor, Claire M. Coleman, Leslie A. Twining, Branko Mitasev, and Kay M. Brummond, J. Comb. Chem. 2006, 8, 368-380.

Computational Insight Concerning Catalytic Decision Points of the Transition Metal Catalyzed [2 + 2 + 1] Cyclocarbonylation Reaction of Allenes

Alexander S. Bayden, Kay M. Brummond, and Kenneth Jordan, Organometallics 2006, 25, 5204-5206.

A Formal Total Synthesis of (-)-FR901483 Using a Tandem Cationic Aza-Cope Rearrangement/Mannich Cyclization Approach

Kay M. Brummond and Sang-phyo Hong  J. Org. Chem200570, 907-916. JOC Most-Accessed Articles January-June, 2005.

Consecutive Rh(I)-Catalyzed Alder-ene/Diels-Alder/Diels-Alder Reaction Sequence Affording Rapid Entry to Polycyclic Compounds

Kay M. Brummond and Lingfeng You, Tetrahedron Symposia-in-Print, Applications of Catalysis in Industry and Academia 2005, 61, 6180-6185.

Allenes and Transition Metals: A Diverging Approach to Heterocycles

Kay M. Brummond and Branko Mitasev, Org. Lett. 20046, 2245-2248.

Rhodium(I)-Catalyzed Ene-Allene Carbocyclization Strategy for the Formation of Azepines and Oxepines

Kay M. Brummond, Hongfeng Chen, Branko Mitasev, and Anthony D. Casarez, Org. Lett. 2004, 6, 2161-2163.

The First Total Synthesis of 15-Deoxy-∆12,14-prostaglandin J­2 and the Unambiguous Assignment of the C14Stereochemistry

Kay M. Brummond, Peter C. Sill, and Hongfeng Chen, Org. Lett. 2004, 6,149-152.

A Rhodium(I)-Catalyzed Formal Allenic Alder-ene Reaction for the Rapid and Stereoselective Assembly of Cross-Conjugated Trienes

Kay M. Brummond, Hongfeng Chen, Peter C. Sill, and Lingfeng You, J. Am. Chem. Soc. 2002, 124, 15186-15187.

A Silicon Tethered Allenic Pauson-Khand Reaction

Kay M. Brummond, Brenden Rickards, Peter C. Sill, and Steven J. Geib, Tetrahedron Lett. 200243, 3735-3738.

An Allenic Pauson-Khand-Type Reaction: A Reversal in π-Bond Selectivity and the Formation of Seven-Membered Rings

Kay M. Brummond, Hongfeng Chen, Kimberly D. Fisher, Angela D. Kerekes, Brenden Rickards, Peter C. Sill, and Steven J. Geib, Org. Lett20024, 1931-1934.

Solid-Phase Synthesis of BRL 49653

Kay M. Brummond and Jianliang Lu, J. Org. Chem. 1999, 64, 1723-1726.

α-Chlorination of Ketones Using p-Toluenesulfonyl Chloride

Kay M. Brummond and Kirsten D. Gesenberg, Tetrahedron Lett199940, 2231-2234.

Polymorphism in Myristoylpalmitoylphosphatidylcholine

Stephanie Tristram-Nagle, Yisrael Isaacson, Yulia Lyatskaya, Yufeng Liu, Kay Brummond, John Katsaras, and John F. Nagle, Chem. Phys. Lipids 1999100, 101-110.

A New Method for the Preparation of Alkynes from Vinyl Triflates

Kay M. Brummond, Kirsten D. Gesenberg, Joseph L. Kent, and Angela D. Kerekes, Tetrahedron Lett199839, 8613-8616.

An Intramolecular Allenic [2 + 2 + 1] Cycloaddition

Kay M. Brummond, Honghe Wan, and Joseph L. Kent, J. Org. Chem1998, 63, 6535-6545.

The Allenic Pauson-Khand Cycloaddition.  Dependence in π-Bond Selectivity on Substrate Structure

Kay M. Brummond and Honghe Wan, Tetrahedron Lett199839, 931-934.

Strategy for the Preparation of Allenes from α,β-Unsaturated and Saturated Ketones via Enol Phosphates

Kay M. Brummond, Elizabeth A. Dingess, and Joseph L. Kent, J. Org. Chem199661, 6096-6097.

A New Allenic Pauson-Khand Cycloaddition for the Preparation of α-Methylene Cyclopentenones

Joseph L. Kent, Honghe Wan, and Kay M. Brummond, Tetrahedron Lett. 199536, 2407-2410.