Publications

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(60) Wenxin Lu, Haote Li, Jan Paul Menzel, Abbigayle E. Cuomo, Andrea M. Nikolic, H. Ray Kelly, Yu Shee, Sanil Sreekumar, Frederic Buono, Jinhua J. Song, Robert H. Crabtree, Victor S. Batista, Timothy R. Newhouse. “Enhanced Ligand Discovery through Generative AI and Latent-Space Exploration: Application to the Mizoroki-Heck Reaction” ChemRxiv. Cambridge: Cambridge Open Engage; 2024.

(59) Yu Shee, Haote Li, Pengpeng Zhang, Andrea M. Nikolic, Wenxin Lu, H. Ray Kelly, Vidhyadhar Manee, Sanil Sreekumar, Frederic Buono, Jinhua J. Song, Timothy R. Newhouse, Victor S. Batista. “Site-Specific Template Gerative Approach for Refrosynthetic Planning”, Nat. Commun. 2024. 15, 7818.

(58) H. Ray Kelly, Sanil Sreekumar, Vidhyadhar Manee, Abbigayle E. Cuomo, Timothy R. Newhouse, Victor S. Batista, Frederic Buono. “Ligand-Based Prinicpal Component Analysis Followed by Ridge Regression: Application to an Asymmetric Negishi Reaction” ACS Catal. 2024. 14(7), 5027-5038.

(57) Alexandra K. Bodnar, Timothy R. Newhouse. “Accessing Z-Enynes via Cobalt-Catalyzed Propargylic Dehydrogenation” Angew. Chem. Int. Ed. 2024.

(56) Alexandra K. Bodnar, Suzanne M. Szewczyk, Yang Sun, Yifeng Chen, Anson X. Huang, Timothy R. Newhouse. “Comprehensive Mechanistic Analysis of Palladium- and Nickel-Catalyzed α,β-Dehydrogenation of Carbonyls via Organozinc Intermediates” J. Org. Chem. 2024, 89(5), 3123-3132.

(55) Abbigayle E. Cuomo, Sebastian Ibarran, Sanil Sreekumar, Haote Li, Jungmin Eun, Jan Paul Menzel, Pengpeng Zhang, Frederic Buono, Jinhua J. Song, Robert H. Crabtree, Victor S. Batista*, Timothy R. Newhouse*. “Feed-Forward Neural Network for Predicting Enantioselectivity of the Asymmetric Negishi Reaction” ACS Cent. Sci. 2023.

(54) Pengpeng Zhang, Timothy R. Newhouse*. “Palladium-Catalyzed Carbonylative Difunctionalization of Unactivated Alkenes Initiated by Unstabilized Enolates” Angew. Chem. Int. Ed. 2023, 62, e202307455.

(53) Daria E. Kim, Yingchuan Zhu, Shingo Harada, Isaiah Aguilar, Abbigayle E. Cuomo, Minghao Wang, Timothy R. Newhouse*. “Total Synthesis of (+)-Shearilicine” J. Am. Chem. Soc. 2023, 8, 4394-4399.

(52) Edward A. deRamon, Venkata R. Sabbasani, Matthew D. Streeter, Yannan Liu, Timothy R. Newhouse, David M. McDonald, David A. Spiegel*. “Pentosinane, a Post-Translational Modification of Human Proteins with Underappreciated Stability” J. Am. Chem. Soc. 2022

(51) Jungmin Eun, Timothy R. Newhouse*. “Computational decoding” Nature Reviews Chemistry, 2022, 6, 168-169

(50) Yannan Liu, Alexander W. Schuppe, Yizhou Zhao, Jaehoo Lee, Timothy R. Newhouse. “Synthesis of (–)-melazolide B, a degraded limonoid, from a natural terpene precursor” Tetrahedron Chem. 1, 2022

(49) Pengpeng Zhang, Jin Wang, Zoe R. Robertson, Timothy R. Newhouse. “Coordination-Controlled Nickel-Catalyzed Benzylic Allylation of Unactivated Electron-Deficient Heterocycles” Angew. Chem. Int. Ed. 2022

(48) Pengpeng Zhang, Timothy R. Newhouse*. “Thiophene, 2-bromo-5-methyl-” Encyclopedia for Reagents in Organic Synthesis 2021, DOI: 10.1002/047084289X.rn02366

(47) Alexander W. Schuppe, Yannan Liu, Yizhou Zhao, Sebastian Ibarraran, David Huang, Emma Wang, Jaehoo Lee, Patrick Loria, Timothy R. Newhouse. “Strategies for the De Novo Synthesis of Highly Substituted Pyridine Scaffolds: Unified Total Synthesis of the Limonoid Alkaloids” Chem, 2022. 8, 2856-2887.

(46) Pengpeng Zhang†, Jungmin Eun†, Masha Elkin, Yizhou Zhao, Rachel L. Cantrell, and Timothy R. Newhouse. “A Neural Network Model Informs Total Synthesis of Clovane Sesquiterpenoids” Nat. Syn. 2023. 2, 527-534.

(45) Alexandra K. Bodnar, Aneta Turlik, David Huang, Will Butcher, Joanna K. Lew, Timothy R. Newhouse. “Preparation of Hindered Aniline CyanH and Application in the Allyl-Ni-Catalyzed α,β-Dehydrogenation of Carbonyls” Org. Synth. 2021, 98, 263-288.

(44) Chang-Yun Shi†, Jungmin Eun†, Timothy R. Newhouse*, Liang Yin* “Copper(I)‐Catalyzed Asymmetric Conjugate 1,6‐, 1,8‐, and 1,10‐Borylation” Angew. Chem. Int. Ed. 2021, xx-xx.

(43) David Huang†, Timothy R. Newhouse. “Dehydrogenative Pd and Ni Catalysis for Total Synthesis” Acc. Chem. Res. 2021, 54, 1118-1130.

(42) Alexander W. Schuppe†, Yannan Liu†, Timothy R. Newhouse. “An Invocation for Computational Evaluation of Isomerization Transforms: Cationic Skeletal Reorganizations as a Case Study” Natural Product Reports, 2021, 38, 510-527.

(41) Diego Olivieri†, David Huang†, Alexandra K. Bodnar, Shijin Yu, Timothy R. Newhouse. “Zinc-mediated anionic cyclization of unstabilized ketone enolates with unactivated alkenes” Tetrahedron 2020, 76.

(40) Yannan Liu, Tina A. Holt, Andrei Kutateladze, Timothy R. Newhouse. “Stereochemical Revision of Xylogranatin F by GIAO and DU8+ NMR Calculations” Chirality, 2020, 32, 515-523.

(39) Pengpeng Zhang, David Huang, Timothy R. Newhouse. “Aryl-Nickel-Catalyzed Benzylic Dehydrogenation of Electron-Deficient Heteroarenes” J. Am. Chem. Soc. 2020 142, 1757-1762.

(38) Pengpeng Zhang, Timothy R. Newhouse. “Oxidation Stepping Stones: α-Oxytriflation Enables Asymmetric Arylation of Amides” Chem. 2019, 5(7), 1690-1692.

(37) David Huang, Diego Olivieri, Yang Sun, Pengpeng Zhang, Timothy R. Newhouse. “Nickel-Catalyzed Difunctionalization of Unactivated Alkenes Initiated by Unstabilized Enolates” J. Am. Chem. Soc. 2019, 141, 16249-16254.

(36) Alexander W. Schuppe†, Yizhou Zhao†, Yannan Liu, Timothy R. Newhouse. “Total Synthesis of (+)-Granatumine A and Related Bislactone Limonoid Alkaloids via a Pyran to Pyridine Interconversion” J. Am. Chem. Soc. 2019, 141, 9191-9126.

(35) Aneta Turlik, Yifeng Chen, Anthony C. Scruse, Timothy R. Newhouse. “Convergent Total Synthesis of Principinol D, a Rearranged Kaurane Diterpenoid” J. Am. Chem. Soc. 2019, 141, 8088-8092.

(34) Joshua E. Zweig, Tongil A. Ko, Junrou Huang, Timothy R. Newhouse. “Effects of π-Extension on Pyrrole Hemithioindigo Photoswitches.” Tetrahedron. 2019, 75(34), 130466.

(33) David Huang, Suzanne M. Szewczyk, Pengpeng Zhang, Timothy R. Newhouse. “Allyl-Nickel Catalysis Enables Carbonyl Dehydrogenation and Oxidative Cycloalkenylation of Ketones” J. Am. Chem. Soc. 2019, 141, 5669–5674.

(32) Daria E. Kim, Joshua E. Zweig, Timothy R. Newhouse. “Total Synthesis of Paspaline A and Emindole PB Enabled by Computational Augmentation of a Transform-Guided Retrosynthetic Strategy” J. Am. Chem. Soc. 2019, 141, 1479–1483.

(31) Masha Elkin†, Anthony C. Scruse†, Aneta Turlik, Timothy R. Newhouse. “Computational and Synthetic Investigation of Cationic Rearrangement in the Putative Biosynthesis of Justicane Triterpenoids” Angew. Chem. Int. Ed. 2019, 58, 1025–1029.

(30) Daria E. Kim, Yingchuan Zhu, Timothy R. Newhouse. “Vinylogous acyl triflates as an entry point to α,β-disubstituted cyclic enones via Suzuki–Miyaura cross-coupling” Org. Biomol. Chem. 2019, 17, 1796–1799.

(29) Rachel A. Coleman, Christine S. Muli, Yizhou Zhao, Atul Bhardwaj, Timothy R. Newhouse, Darci J. Trader. “Analysis of chain length, substitution patterns, and unsaturation of AM-404 derivatives as 20S proteasome stimulators” Bioorganic Med. Chem. Lett. 2019, 29, 420–423.

(28) Masha Elkin, Timothy R. Newhouse. “Computational chemistry strategies in natural product synthesis” Chem. Soc. Rev. 2018, 47, 7830–7844.

(27) Hai-Jun Zhang, Alexander W. Schuppe, Shi-Tao Pan, Jin-Xiang Chen, Bo-Ran Wang, Timothy R. Newhouse,* and Liang Yin.* “Copper-Catalyzed Vinylogous Aerobic Oxidation of Unsaturated Compounds with Air” J. Am. Chem. Soc. 2018, 140, 5300-5310.

(26) Suzanne M. Szewczyk, Yizhou Zhao, Holt Sakai, Pascal Dube, Timothy R. Newhouse. “α,β-Dehydrogenation of esters with free O-H and N-H functionalities via allyl-palladium catalysis” Tetrahedron 2018, 74, 3293-3300.

(25) Alexander W. Schuppe, David Huang, Yifeng Chen, Timothy R. Newhouse. “Total Synthesis of (–)-Xylogranatopyridine B via a Palladium-Catalyzed Oxidative Stannylation of Enones” J. Am. Chem. Soc. 2018, 140, 2062-2066.

(24) David Huang, Yizhou Zhao, Timothy R. Newhouse. Synthesis of Cyclic Enones by Allyl-Palladium-Catalyzed α,β-Dehydrogenation” Org. Lett. 2018, 20, 684–687.

(23) Yizhou Zhao, Yifeng Chen, Timothy R. Newhouse. “Allyl-Palladium Catalyzed α,β-Dehydrogenation of Carboxylic Acids via Enediolates” Angew. Chem. Int. Ed. 2017, 56, 13122-13125.

(22) Joshua E. Zweig, Timothy R. Newhouse. “Isomer-Specific Hydrogen Bonding as a Design Principle for Bidirectionally Quantitative and Redshifted Hemithioindigo Photoswitches” J. Am. Chem. Soc. 2017, 139, 10956-10959.

(21) Gong Xu, Masha Elkin, Dean Tantillo, Timothy R. Newhouse,* Thomas Maimone.* “Traversing Biosynthetic Carbocation Landscapes in the Total Synthesis of Andrastin and Terretonin Meroterpenes” Angew. Chem. Int. Ed. 2017, 56, 12498-12502.

(20) Yifeng Chen, David Huang†, Yizhou Zhao†, Timothy R. Newhouse. “Allyl-Palladium Catalyzed Ketone Dehydrogenation Enables Telescoping with Enone α,β-Vicinal Difunctionalization” Angew. Chem. Int. Ed. 2017, 56, 8258-8262.

(19) Joshua E. Zweig, Daria E. Kim, Timothy R. Newhouse. “Methods Utilizing First-Row Transition Metals in Natural Product Total Synthesis” Chem. Rev. 2017, 117, 11680-11752.

(18) Alexander W. Schuppe, James M. Cabrera, Catherine L. B. McGeoch, Timothy R. Newhouse.* “Scalable synthesis of enaminones utilizing Gold’s reagents” Tetrahedron 2017, 73, 3643–3651.

(17) Masha Elkin, Suzanne M. Szewczyk, Anthony C.Scruse, Timothy R. Newhouse. “Total Synthesis of (±)-Berkeleyone A” J. Am. Chem. Soc. 2017, 139, 1790-1793.

(16) Alexander W. Schuppe, Timothy R. Newhouse. “Assembly of the Limonoid Architecture by a Divergent Approach: Total Synthesis of (±)-Andirolide N via (±)-8α-Hydroxycarapin” J. Am. Chem. Soc. 2017, 139, 631-634.

Featured in: Contemporary Synthetic Chemistry in Drug Discovery

(15) David Huang, Alexander W. Schuppe, Michael Z. Liang and Timothy R. Newhouse. “Scalable procedure for the fragmentation of hydroperoxides mediated by copper and iron tetrafluoroborate salts.” Org. Biomol. Chem. 2016, 14, 6197.

(14) Yifeng Chen, Aneta Turlik, Timothy R. Newhouse. “Amide α,β-Dehydrogenation Using Allyl-Palladium Catalysis and a Hindered Monodentate Anilide.” J. Am. Chem. Soc. 2016, 138,1166.

(13) Aneta Turlik, Yifeng Chen, Timothy R. Newhouse. “Dehydrogenation Adjacent to Carbonyls Using Pd-Allyl Intermediates.” Synlett 2016, 27, 331.

(12) Yifeng Chen, Justin P. Romaire, Timothy R. Newhouse. “Palladium-Catalyzed α,β-Dehydrogenation of Esters and Nitriles.” J. Am. Chem. Soc. 2015, 137, 5875.

Timothy R. Newhouse before Yale:

(11) T. R. Newhouse, P. Kaib, A. Gross, E. J. Corey. “Versatile Approaches for the Synthesis of Chiral Fused-Ring g-Lactones Utilizing Cyclopropane Intermediates.” Org. Lett. 2013, 15, 1591–1593.

(10) T. R. Newhouse, X. Li, M. M. Blewett, C. M. C. Whitehead, E. J. Corey. “A Tetradentate Ligand for the Enantioselective Ti(IV)-Promoted Oxidation of Sulfides to Sulfoxides: Origin of Enantioselectivity.” J. Am. Chem. Soc. 2012, 134, 17354 – 17357.

(9) L. Zou, R. S. Paton, A. Eschenmoser, T. R. Newhouse, P. S. Baran, K. N. Houk. “Enhanced Reactivity in Dioxirane C-H Oxidations via Strain Release.” J. Org. Chem. 2013, 78, DOI: 10.1021/jo400350v

(8) T. Newhouse, P. S. Baran. “If C-H Bonds Could Talk: Selective C-H Bond Oxidation.” Angew. Chem. Int. Ed. 2011, 50, 3362 – 3374.

(7) K. Foo, T. Newhouse, I. Mori, H. Takayama, P. S. Baran. “Total Synthesis Guided Structure Elucidation of (+)-Psychotetramine.” Angew. Chem. Int. Ed. 2011, 50, 2716 – 2719.

(6) T. Newhouse, C. A. Lewis, K. J. Eastman, P. S. Baran. “Scalable Total Syntheses of N-Linked Tryptamine Dimers by Direct Indole-Aniline Coupling: Psychotrimine and Kapakahines B and F.” J. Am.Chem. Soc. 2010, 132, 7119 – 7137.

(5) M. A. Schallenberger, T. Newhouse, P. S. Baran, F. E. Romesberg, “The Psychotrimine Natural Products Have Antibacterial Activity Against Gram-Positive Bacteria and Act Via Membrane Disruption.” J. Antibiot. 2010, 63, 685 – 687.

(4) T. Newhouse, P. S. Baran, R. W. Hoffmann. “The Economies of Synthesis.” Chem. Soc. Rev. 2009, 38, 3010 – 3021.

(3) T. Newhouse, C. A. Lewis, P. S. Baran. “Enantiospecific Total Syntheses of Kapakahines B and F.” J. Am. Chem. Soc. 2009, 131, 6360 – 6361.

(2) T. Newhouse, P. S. Baran. “Total Synthesis of (±)-Psychotrimine.” J. Am. Chem. Soc. 2008, 130, 10886 – 10887.

(1) R. I. Goldstein, R. Guo, C. Hughes, D. P. Maurer, T. Newhouse, T. J. Sisto, R. R. Conry, S. L. Price, D. M. Thamattoor. “Concomitant conformational dimorphism in 1,2-bis(9-anthryl)acetylene” CrystEngComm 2015, 17, 4877 – 4882.