Publications

Newhouse Group at Yale:

25) 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 InterconversionJ. Am. Chem. Soc. 2019, Articles ASAP. DOI:10.1021/jacs.9b04508

24) Aneta Turlik, Yifeng Chen, Anthony C. Scruse, Timothy R. Newhouse. “Convergent Total Synthesis of Principinol D, a Rearranged Kaurane DiterpenoidJ. Am. Chem. Soc. 2019, Articles ASAP. DOI:10.1021/jacs.9b03751

 

23) Joshua E. Zweig, Tongil A. Ko, Junrou Huang, Timothy R. Newhouse.* “Effects of π-Extension on Pyrrole Hemithioindigo Photoswitches.” ChemRxiv. 2019, DOI:10.26434/chemrxiv.7868927

22) 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. DOI: 10.1021/jacs.9b02552.

Feature in X-MOL

Synfacts: α,β-Dehydrogenation and Oxidative Cycloalkenylation Catalyzed by Nickel

21) 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. DOI: 10.1021/jacs.8b13127.

Featured in C&EN News: Computation helps chemists shorten synthesis of natural product

Featured in Chemistry World: Computation trick cuts natural product synthesis from 27 to nine steps

Featured in YaleNews: Synthesizing natural products with a computational step saver

Featured in Computational Chemistry Highlights: Computationally Augmented Retrosynthesis: Total Synthesis of Paspaline A and Emindole PB

Synfacts: Synthesis of Paspaline A and Emindole PB

20) 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. DOI: 10.1002/anie.201810566.

19) 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. 201917, 1796–1799. DOI: 10.1039/c8ob02573h.

18) 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. DOI:10.1016/j.bmcl.2018.12.030

 

17) Masha Elkin, Timothy R. Newhouse. “Computational chemistry strategies in natural product synthesis” Chem. Soc. Rev. 201847, 7830–7844. DOI: 10.1039/C8CS00351C

 Cover feature

16) 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 AirJ. Am. Chem. Soc. 2018140, 5300-5310. DOI: 10.1021/jacs.8b01886. 

15) 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. DOI: 10.1016/j.tet.2018.02.028.

14) 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. Soc2018140, 2062-2066. DOI: 10.1021/jacs.7b13189.

Highlighted by Synfacts, May 2018

13) David Huang, Yizhou Zhao, Timothy R. Newhouse.* Synthesis of Cyclic Enones by Allyl-Palladium-Catalyzed α,β-Dehydrogenation” Org. Lett201820684–687. DOI: 10.1021/acs.orglett.7b03818.

Highlighted by Synfacts, April 2018

12) Yizhou Zhao, Yifeng Chen, Timothy R. Newhouse.* “Allyl-Palladium Catalyzed α,β-Dehydrogenation of Carboxylic Acids via EnediolatesAngew. Chem. Int. Ed. 2017, 56, 13122-13125. DOI: 10.1002/anie.201706893.

Highlighted by Synfacts, November 2017

11) Joshua E. Zweig, Timothy R. Newhouse.* “Isomer-Specific Hydrogen Bonding as a Design Principle for Bidirectionally Quantitative and Redshifted Hemithioindigo PhotoswitchesJ. Am. Chem. Soc. 2017, 139, 10956-10959. DOI: 10.1021/jacs.7b04448.

10) Gong Xu, Masha Elkin, Dean Tantillo, Timothy R. Newhouse,* Thomas Maimone.* “Traversing Biosynthetic Carbocation Landscapes in the Total Synthesis of Andrastin and Terretonin MeroterpenesAngew. Chem. Int. Ed. 2017, 56, 12498-12502. DOI: 10.1002/anie.201705654.

Organometallic Chemistry

 

9) Yifeng Chen, David Huang†, Yizhou Zhao†, Timothy R. Newhouse.* “Allyl-Palladium Catalyzed Ketone Dehydrogenation Enables Telescoping with Enone α,β-Vicinal DifunctionalizationAngew. Chem. Int. Ed. 2017, 56, 8258-8262. DOI: 10.1002/anie.201704874

8) Joshua E. Zweig, Daria E. Kim, Timothy R. Newhouse.* “Methods Utilizing First-Row Transition Metals in Natural Product Total SynthesisChem. Rev. 2017, 117, 11680-11752. DOI: 10.1021/acs.chemrev.6b00833.

7)  Alexander W. Schuppe, James M. Cabrera, Catherine L. B. McGeoch, Timothy R. Newhouse.* “Scalable synthesis of enaminones utilizing Gold’s reagentsTetrahedron 2017, 73, 3643–3651. DOI: 10.1016/j.tet.2017.03.092.

Part of Tetrahedron Young Investigator Award 2017; A Special Issue in Honor of Professor Ang Li, June 2017

6) Masha Elkin, Suzanne M. Szewczyk, Anthony C.Scruse, Timothy R. Newhouse.* “Total Synthesis of (±)-Berkeleyone A” J. Am. Chem. Soc. 2017, 139, 1790-1793. DOI: 10.1021/jacs.6b12914.

5) 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. DOI: 10.1021/jacs.6b12268.

Highlighted by Synfacts, April 2017

4) 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, 6197DOI: 10.1039/c6ob00941g.

This article is part of themed collection: Contemporary Synthetic Chemistry in Drug Discovery

Graphical abstract: Scalable procedure for the fragmentation of hydroperoxides mediated by copper and iron tetrafluoroborate salts

3) 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, 138,1166DOI: 10.1021/jacs.5b12924.

Highlighted by Synfacts, March 2016

2) Aneta Turlik, Yifeng Chen, Timothy R. Newhouse.* “Dehydrogenation Adjacent to Carbonyls Using Pd-Allyl Intermediates.” Synlett 2016, 27, 331. DOI: 10.1055/s-0035-1561282.

1) Yifeng Chen, Justin P. Romaire, Timothy R. Newhouse.* “Palladium-Catalyzed α,β-Dehydrogenation of Esters and Nitriles.”  J. Am. Chem. Soc. 2015137, 5875. DOI: 10.1021/jacs.5b02243.

Highlighted in OPRD’s “Some Items of Interest to Process R&D Chemists and Engineers,” July 2015

ja-2015-02243m_0003

TRN before Yale:

10) 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.

9) 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.

8) 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

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

6) 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.

5) 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.

4) 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.

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

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

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