Stanford University

Publications

2020

 

Discovery of a Selective, State-Independent Inhibitor of NaV1.7 by Modification of Guanidinium Toxins

Pajouhesh, H.; Beckley, J. T.; Delwig, A.; Hajare, H. S.; Luu, G.; Monteleone, D.; Zhou, X.; Ligutti, J.; Amagasu, S.; Moyer, B. D.; Yeomans, D.; Du Bois, J.; Mulcahy, J. V.

Scientific Reports 2020, 10, article number 14791.

 

Electrochemical Ruthenium-Catalyzed C–H Hydroxylation of Amine Derivatives in Aqueous Acid

Robinson, S. G.; Mack, J. B. C.; Alektiar, S. N.; Du Bois, J.; Sigman, M. S.

Org. Lett. 202022, 70607063.

 

Dynamical model of the CLC-2 ion channel reveals conformational changes associated with selectivity-filter gating

McKiernan, K. A.; Koster, A. K.; Maduke, M.; Pande, V. S.

PLOS Computational Biology 202016, e1007530.

 

Intermolecular sp3 C-H amination for the synthesis of saturated azacycles (Org. Lett. cover article)

Betz, K. N.; Chiappini, N. D.; Du Bois, J. 

Org. Lett. 2020, 22, 16871691.

 

Veratridine: A Janus-Faced Modulator of Voltage-Gated Sodium Ion Channels

Craig, R. A. II; Garrison, C. E.; Nguyen, P. T.; Yarov-Yarovoy, V.; Du Bois, J.

ACS Chem. Neurosci 2020, 11, 418426.

 

Development and validation of a potent and specific inhibitor provides evidence for the CLC-2 chloride channel as a potential epilepsy target

Koster, A. K.; Reese, A. L.; Kuryshev, Y.; Wen, X.; Lu, A. C.; McKiernan, K. A.; Gray, E. E.; Wu, C.; Beenhakker, M. P.; Huguenard, J. R.; Maduke, M.; Du Bois, J.

BioRxiv 2020.

 

C-H Functionalization Reaction Manual

West, J. G.; Morton, D.; Bedell, T. A.; Mack, J. B. C.

Sigma Aldrich / Merck KGaA 2020.

2019

Structure of the saxiphilin:saxitoxin (STX) complex reveals a convergent molecular recognition strategy for paralytic toxins

Yen, T.-J.; Lolicato, M.; Thomas-Tran, R.; Du Bois, J.; Minor, D. L., Jr.

Science Advances 2019, 5, eaax2650.

 

Challenges and Opportunities for Therapeutics Targeting the Voltage-Gated Sodium Channel Isoform NaV1.7

Mulcahy, J. V.; Pajouhesh, H.; Beckley, J. T.; Delwig, A.; Du Bois, J.; Hunter, J. C.

J. Med. Chem. 2019, 62, 19, 86958710.

 

Divergent Synthesis of Natural Derivatives of (+)​-​Saxitoxin Including 11-​Saxitoxinethanoic Acid

Walker, J. R.; Merit, J. E.; Thomas-Tran, R.; Tang, D. T. Y.; Du Bois, J.

Angew. Chem. Int. Ed. 2019, 58, 16891693.

 

Mechanistic Study of Ruthenium-​Catalyzed C-​H Hydroxylation Reveals an Unexpected Pathway for Catalyst Arrest

Mack, J. B. C.; Walker, K. L.; Robinson, S. G.; Zare, R. N.; Sigman, M. S.; Waymouth, R. M.; Du Bois, J.

J. Am. Chem. Soc. 2019, 141, 972980.

2018

Intermolecular sp3 C-H Amination of Complex Molecules

Chiappini, N. D.; Mack, J. B. C.; Du Bois, J.

Angew. Chem. Int. Ed. 2018, 57, 4956–4959

 

Site-Selective Bromination of sp3 C-H Bonds

Sathyamoothi, S.; Banerjee, S.; Du Bois, J.; Burns, N. Z.; Zare, R. N.

Chem. Sci. 2018, 9, 100–104.

 

Cyanthiwigin Natural Product Core as a Complex Molecular Scaffold for Comparative Late-​Stage C-​H Functionalization Studies

Kim, K. E.; Adams, A. M.; Chiappini, N. D.; Du Bois, J.; Stoltz, B. M.

J. Org. Chem. 2018, 83, 30233033.

 

Synthetic Studies Toward Pactamycin Highlighting Oxidative C–H and Alkene Amination Technologies

Su, J. Y.; Olsen, D. E.; Ting, S. I.; Du Bois, J.

J. Org. Chem. 2018, 83, 71217134.

 

A selective class of inhibitors for the CLC-Ka chloride ion channel

Koster, A. K.; Wood, C. A. P.; Thomas-Tran, R.; Chavan, T. S.; Alqvist, J.; Choi, K.-H.; Du Bois, J.; Maduke, M.

Proc. Natl. Acad. Sci. USA 2018, 115, 49004909.

 

Rhodium-​Catalyzed C-​H Amination: A Case Study of Selectivity in C-​H Functionalization Reactions

Mack, J. B. C.; Bedell, T. A.; DeLuca, R. J.; Hone, G. A. B.; Roizen, J. L.; Cox. C. T.; Sorensen, E. J.; Du Bois, J.

J. Chem. Educ. 2018, 95, 22432248.

 

C-​H Hydroxylation in Paralytic Shellfish Toxin Biosynthesis

Lukowski, A. L.; Ellinwood, D. C.; Hinze, M. E.; DeLuca, R. J.; Du Bois, J.; Hall, S.; Narayan, A. R. H.

J. Am. Chem. Soc. 2018, 140, 1186311869.

 

2017

Ruthenium-Catalyzed C-H Hydroxylation in Aqueous Acid Enables Selective Functionalization of Amine Derivatives.

Mack, J. B. C. M.; Gipson, J. D.; Du Bois, J.; Sigman, M. S.

J. Am. Chem. Soc. 2017, 139, 9503–9506.

 

Mechanistic Analysis of a Copper-Catalyzed C–H Oxidative Cyclization of Carboxylic Acids.

Banerjee, S.; Sathyamoorthi, S.; Du Bois, J.; Zare, R. N.

Chem. Sci. 2017, 8, 7003–7008.

2016

Rh2(II,III) Catalysts with Chelating Carboxylate and Carboxamidate Supports: Electronic Structure and Nitrene Transfer Reactivity.

Varela-Alvarez, A.;Yang, T.; Jennings, H.; Kornecki, K. P.; Macmillan, S. N.; Lancaster, K. M.; Mack, J. B. C.; Du Bois, J.; Berry, J. F.; Musaev, D. G.

J. Am. Chem. Soc. 2016, 138, 2327–2341.

 

Synthesis of the Paralytic Shellfish Poisons (+)-Gonyautoxin 2, (+)-Gonyautoxin 3, and (+)-11,11-Dihroxysaxitoxin

Mulcahy, J. V.; Walker, J. R.; Merit, J. E.; Whitehead, A.; Du Bois, J.

J. Am. Chem. Soc. 2016, 138, 5994–6001.

 

Mutant cycle analysis with modified saxitoxins reveals specific interactions critical to attaining high-affinity inhibition of hNav1.7.

Thomas-Tran, R.; Du Bois, J.

Proc. Natl. Acad. Sci. USA 2016, 113, 5856–5861.

 

Manganese (II)/Picolinic Acid Catalyst System for Epoxidation of Olefins.

Moretti, R. A.; Du Bois, J.; Stack, T. D. P.

Org. Lett. 2016, 18, 2528–2531.

 

Inhibition of Sodium Ion Channel Function with Truncated Forms of Batrachotoxin.

Toma, T.; Logan, M. M.; Menard, F.; Devlin, A. S.; Du Bois, J.

ACS Chem. Neruosci. 2016, 7, 14631468.

 

Asymmetric Synthesis of Batrachotoxin: Enantiomeric Toxins Show Functional Divergence against Nav.

Logan, M. M.; Toma, T.; Thomas-Tran, R.; Du Bois, J.

Science 2016, 354, 865869.

 

Copper-Catalyzed Oxidative Cyclization of Carboxylic Acids.

Sathyamoorthi, S.; Du Bois, J.

Org. Lett. 2016, 18, 63086311.

2015

An Expedient Synthesis of Maraviroc (UK-427,857) via C-H Functionalization.

Bedell, T. A.; Hone, G. A. B.; Du Bois, J.; Sorensen, E. J.

Tett. Lett. 2015, 56, 3620–3623.

 

Comparative Study of the Limitations in Atom-Transfer C-H Oxidations

Adams, A. M.; Du Bois, J.; Malik, H. A.

Org. Lett. 2015, 17, 6066–6069.

2014

Organocatalytic C–H hydroxylation with Oxone® enabled by an aqueous fluoroalcohol solvent system.

Adams, A. M.; Du Bois, J.

Chem. Sci. 2014, 5, 656659.

 

Non-Directed Allylic C-H Acetoxylation in the Presence of Lewis Basic Heterocycles.

Malik, H. A.; Taylor, B. L. H.; Kerrigan, J. R.; Grob, J. E.; Houk, K.; Du Bois, J.; Hamann, L.; Patterson, A. W.

Chem. Sci. 2014, 5, 23522361.

 

Analyzing Site Selectivity in Rh2(esp)2-Catalyzed Intermolecular C-H Amination Reactions.

Bess, E. N.; DeLuca, R. J.; Tindall, D. J.; Oderinde, M. S.; Roizen, J. L.; Du Bois, J.; Sigman, M. S.

J. Am. Chem. Soc. 2014, 136, 57835789.

 

Visualizing Dermal Permeation of Sodium Channel Modulators by Mass Spectrometric Imaging

Eberlin, L. S.; Mulcahy, J. V.; Tzabazis, A.; Zhang, J.; Liu, H.; Logan, M. M.; Roberts, H. J.; Lee, G. K; Yeomans, D. C.; Du Bois, J.; Zare, R. N.

J. Am. Chem. Soc. 2014, 136, 64016405.

 

Saxitoxin

Thottumkara, A. P.; Parsons, W. H.; Du Bois, J.

Angew. Chem. Int. Ed. 2014, 53, 57605784.

 

Speciation and Decomposition Pathways of Ruthenium Catalysts used for Selective C-H Hydroxylation.

Flender, C.; Adams, A. M.; Roizen, J. L.; McNeil, E.; Du Bois, J.; Zare, R. N.

Chem. Sci. 2014, 5, 3309–3314.

 

Vicinal Diamination of Alkenes under Rh-Catalysis.

Olson, D. E.; Su, J. Y.; Roberts, D. A.; Du Bois, J.

J. Am. Chem. Soc. 2014, 136, 13506–13509.

2013

Modular Synthesis of the Pentacyclic Core of Batrachotoxin and Select Batrachotoxin Analogue Designs

Devlin, A. S.; Du Bois, J.

Chem. Sci. 2013, 4, 10591063.

 

Carbocyclization of Unsaturated Thioesters under Palladium Catalysis

Thottumkara, A. P.; Kurokawa, T.; Du Bois, J.

Chem. Sci. 2013, 4, 26862689.

 

Maleimide Conjugates of Saxitoxin as Covalent Inhibitors of Voltage-Gated Sodium Channels

Parsons, W. H.; Du Bois, J.

J. Am. Chem. Soc. 2013, 135, 1058210585.

 

Selective Intermolecular Amination of C–H Bonds at Tertiary Carbon Centers

Roizen, J. L.; Zalatan, D. N.; Du Bois, J.

Angew. Chem. Int. Ed. 2013, 52, 1134311346.

 

The Stanford Institute for Chemical Biology

Chen, J. K.; Du Bois, J.; Glenn, J.; Herschlag, D.; Khosla, C.

ACS Chem. Biol. 2013, 8, 18601861.

 

A 18F-Labeled Saxitoxin Derivative for in Vivo PET-MR Imaging of Voltage-Gated Sodium Channel Expression Following Nerve Injury

Hoehne, A.; Behera, D.; Parsons, W. H.; James, M. L.; Shen, B.; Borgohain, P.; Bodapati, D.; Prabhakar, A.; Gambhir, S. S.; Yeomans, D. C.; Biswal, S. Chin, F. T.; Du Bois, J.

J. Am. Chem. Soc. 2013, 135, 1801218015.

2012

Catalytic C–H Oxidation by a Triazamacrocyclic Ruthenium Complex

McNeill, E.; Du Bois, J.

Chem. Sci. 2012, 3, 18101813.

 

Metal-Catalyzed Nitrogen-Atom Transfer Methods for the Oxidation of Aliphatic C–H Bonds

Roizen, J. L.; Harvey, M. E.; Du Bois, J.

Acc. Chem. Res. 2012, 45, 911922.

 

Fluorescent Saxitoxins for Live Cell Imaging of Voltage-gated Sodium Ion Channels Beyond the Optical Diffraction Limit

Ondrus, A. E.; Lee, H.-l. D.; Iwanaga, S.; Parsons, W. H.; Andresen, B. M.; Moerner, W. E.; Du Bois, J.

Chem. Biol. 2012, 19, 902912.

 

Marked Difference in Saxitoxin and Tetrodotoxin Affinities for the Human Nociceptive Voltage-gated Sodium Channel (NaV1.7)

Walker, J. R.; Novick, P.; Parsons, W. A.; McGregor, M.; Zablocki, J.; Pande, V. S.; Du Bois, J.

Proc. Natl. Acad. Sci. USA 2012, 109, 1810218107.

 

Capturing Fleeting Intermediates in a Catalytic C–H Amination Reaction Cycle

Perry, R. H.; Cahill III, T. J.; Roizen, J. L.; Du Bois, J.; Zare, R. N.

Proc. Natl. Acad. Sci. USA 2012, 109, 1829518299.

 

A Designed Inhibitor of a CLC Antiporter Blocks Function Through a Unique Binding Mode

Howery, A. E; Elvington, S.; Abraham, S. J.; Choi, K.-H.; Philips, S.; Ryan, C. M.; Sanford, R. L.; Simpson-Dworschak, S.; Almqvist, J.; Tran, K.; Chew, T. A.; Zachariae, U.; Andersen, O. S.; Whitelegge, J.; Matulef, K.; Du Bois, J.; Maduke, M.

Chem. Biol. 2012, 19, 14601470.

 

Synthesis of Differentially Substituted 1,2-Diamines through Advances in C-H Amination Technology

Olson, D. E.; Roberts, D. A.; Du Bois, J.

Org. Lett. 2012, 14, 61746177.

 

2011

Rhodium-Catalyzed C–H Amination – An Enabling Method for Chemical Synthesis

Du Bois, J.

Org. Process Res. Dev. 2011, 15, 758762.

 

Synthesis and Reactivity of Unique Heterocyclic Structures en route to Substituted Diamines

Olson, D. E.; Maruniak, A.; Malhotra, S.; Trost, B. M.; Du Bois, J.

Org. Lett. 2011, 13, 33363339.

 

A Diruthenium Catalyst for Selective, Intramolecular Allylic C–H Amination: Reaction Development and Mechanistic Insight Gained Through Experiment and Theory

Harvey, M. E.; Musaev, D. G.; Du Bois, J.

J. Am. Chem. Soc. 2011, 133, 1720717216.

 

2010

Metal-Catalyzed Oxidations of C–H to C–N Bonds.

Zalatan, D. N.; Du Bois, J.

Top. Curr. Chem. 2010, 292, 347378.

 

Ruthenium-Catalyzed Hydroxylation of Unactivated 3° C–H Bonds

McNeill, E.; Du Bois, J.

J. Am. Chem. Soc. 2010, 132, 1020210204.

 

2009

Oxidative Cyclization of Sulfamate Esters Using NaOCl – A Metal-Mediated Hoffman-Löffler-Freytag Reaction

Zaltan, D. N.; Du Bois, J.

Synlett (cluster on C–H activation) 2009, 143146.

 

A Mechanistic Analysis of the Rh-Catalyzed Intramolecular C–H Amination Reaction

Williams Fiori, K.; Espino, C. G.; Brodsky, B. H.; Du Bois, J.

Tetrahedron (special edition honoring Tetrahedron Young Investigator) 2009, 65, 30423051.

 

Asymmetric Synthesis of Diamine Derivatives via Sequential Palladium and Rhodium Catalysis

Trost, B. M.; Malhotra, S.; Olson. D. E.; Maruniak, A.; Du Bois, J.

J. Am. Chem. Soc. 2009, 131, 41904191.

 

Synthesis of 1,3-Diamines Through Rhodium-Catalyzed C–H Insertion

Kurokawa, T.; Kim, M.; Du Bois, J.

Angew. Chem. Int. Ed. 2009, 48, 27772779.

 

A Stereoselective Synthesis of the Bromopyrrole Natural Product (–)-Agelastatin A

Wehn, P. M.; Du Bois, J.

Angew. Chem. Int. Ed. 2009, 48, 38023805.

 

C–H Hydroxylation Using a Heterocyclic Catalyst and Aqueous H2O2

Litvinas, N. D.; Du Bois, J.

Angew. Chem. Int. Ed. 2009, 48, 45134516.

 

Understanding the Differential Performance of Rh2(esp)2 as a Catalyst for C–H Amination

Zalatan, D. N.; Du Bois, J.

J. Am. Chem. Soc. 2009, 131, 75587559.

 

De Novo Synthesis of Modified Saxitoxins for Sodium Ion Channel Study

Andresen, B. A.; Du Bois, J.

J. Am. Chem. Soc. 2009, 131, 1252412525.

 

2008

Discovery of Potent CLC Chloride Channel Inhibitors

Matulef, K.; Howery, A. E.; Tan, L.; Kobertz, W. R.; Du Bois, J.; Madduke, M.

ACS Chem. Bio. 2008, 3, 419428.

 

A Chiral Rhodium Carboxamidate Catalyst for Enantioselective C–H Amination

Zalatan, D. N.; Du Bois, J.

J. Am. Chem. Soc. 2008, 130, 92209221.

 

Catalytic C–H Amination for the Preparation of Substituted 1,2-Diamines

Olson, D. E.; Du Bois, J.

J. Am. Chem. Soc. 2008, 130, 1124811249.

 

A Stereoselective Synthesis of (+)-Gonyautoxin 3

Mulcahy, J. V.; Du Bois, J.

J. Am. Chem. Soc. 2008, 130, 1263012631.

 

2007

Catalytic Intermolecular Amination of C–H Bonds: Method Development and Mechanistic Insights

Williams Fiori, K.; Du Bois, J.

J. Am. Chem. Soc. 2007, 129, 562568.

 

(+)-Saxitoxin: A First and Second Generation Stereoselective Synthesis

Fleming, J. J.; McReynolds, M. D; Du Bois, J.

J. Am. Chem. Soc. 2007, 129, 99649975.

 

γ-Sultone Formation Through Rh-Catalyzed C–H Insertion.

Wolckenhauer, S. A.; Devlin, A. S.; Du Bois, J.

Org. Lett. 2007, 9, 43634366.

 

C–H Amination in Synthesis: An Approach to the Assembly of the B/C/D Ring System of Aconitine

Conrad, R. M.; Du Bois, J.

Org. Lett. 2007, 9, 54655468.

2006

Expanding the Substrate Scope of C–H Amination Reactions: Oxidative Cyclization of Urea and Guanidine Derivatives

Kim, M.; Mulcahy, J. V.; Espino, C. G.; Du Bois, J.

Org. Lett. 2006, 8, 10731076.

 

A Synthesis of (+)-Saxitoxin

Fleming, J. J.; Du Bois, J.

J. Am. Chem. Soc. 2006, 128, 39263927.

 

Rh-Catalyzed Alkene Oxidation: A Highly Efficient Process for Preparing N-Alkoxysulfonyl Aziridines

Guthikonda, K.; Wehn, P. M.; Caliando, B. J.; Du Bois, J.

Tetrahedron (special edition honoring Tetrahedron Young Investigator) 2006, 62, 1133111342.

 

Entrapment of a Dirhodium Tetracarboxylate Unit Inside the Aromatic Bowl of a Calix[4]arene: Unique Catalysts for C–H Amination

Brodsky, B. H.; Du Bois, J.

Chem. Comm. 2006, 47154717.

 

2005

In Modern Rhodium-Catalyzed Organic Reactions

Espino, C. G.; Du Bois, J.

Ed.: P. A. Evans, Wiley-VCH Verlag, Weinheim 2005, pp 379416.

 

Rhodium Catalyzed C–H Amination: Versatile Methodology for the Selective Preparation of Amines and Amine Derivatives

Du Bois, J.

Chemtracts. Org. Chem. 2005, 18, 113.

 

Exploring New Uses for C–H Amination: Ni-Catalyzed Cross Coupling of Cyclic Sulfamates

Wehn, P. M.; Du Bois, J.

Org. Lett. 2005, 7, 46854688.

 

Oxaziridine-Mediated Hydroxylation of Unactivated 3° C–H Bonds Using Hydrogen Peroxide

Brodsky, B. H.; Du Bois, J.

J. Am. Chem. Soc. 2005, 127, 1539115393.

2004

Deacylative Oxidation Strategy for the Preparation of a-Functionalized Carbonyls

Brodsky, B. H.; Du Bois, J.

Org. Lett. 2004, 6, 26192621.

 

Rh-Catalyzed Amination of Ethereal α-C–H Bonds: A Versatile Strategy for the Synthesis of Complex Amines

Williams Fiori, K.; Fleming, J. J.; Du Bois, J.

Angew. Chem. Int. Ed. 2004, 43, 43494352.

 

Expanding the Scope of C–H Amination Through Catalyst Design

Espino, C. G.; Williams Fiori, K.; Kim, M.; Du Bois, J.

J. Am. Chem. Soc. 2004, 126, 1537815379.

 

2003

Novel Iminium Ion Equivalents Prepared Through C–H Oxidation for the Stereocontrolled Synthesis of Functionalized Propargylic Amine Derivatives

Fleming, J. J.; Williams Fiori, K.; Du Bois, J.

J. Am. Chem. Soc. 2003, 125, 20282029.

 

A Stereoselective Synthesis of (–)-Tetrodotoxin

Hinman, A.; Du Bois, J.

J. Am. Chem. Soc. 2003, 125, 1151011511.

 

Stereochemical Models for Rh-Catalyzed Amination Reactions of Chiral Sulfamates

Wehn, P. M.; Lee, J.; Du Bois, J.

Org. Lett. 2003, 5, 48234826.

 

2002

Stereoselective Organozinc Addition Reactions to 1,2–Dihydropyrans for the Assembly of Complex Pyran Structures

Steinhuebel, D. P.; Fleming, J. J.; Du Bois, J.

Org. Lett. 2002, 4, 293–295.

 

Enantioselective Synthesis of the Bromopyrrole Alkaloids Manzacidin A and C by Stereospecific C–H Bond Oxidation

Wehn, P. M.; Du Bois, J..

J. Am. Chem. Soc. 2002, 124, 1295012951

 

A Unique and Highly Efficient Method for Catalytic Olefin Aziridination

Guthikonda, K.; Du Bois, J.

J. Am. Chem. Soc. 2002, 124, 1367213673.

 

2001

A Rh-Catalyzed C–H Insertion Reaction for the Oxidative Conversion of Carbamates to Oxazolidinones

Espino, C. G.; Du Bois, J.

Angew. Chem., Int. Ed. Engl. 2001, 40, 598–600.

 

Synthesis of 1,3–Difunctionalized Amine Derivatives through Selective C–H Bond Oxidation

Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J.

J. Am. Chem. Soc. 2001, 123, 6935–6936.