Publications-Junichiro Yamaguchi-

PUBLICATION

Associate Professor 

[60] Decarbonylative organoboron cross-coupling of esters by nickel catalysis

Kei Muto, Junichiro Yamaguchi, Djamaladdin G. Musaev and Kenichiro Itami

Nature. Commun. 20156, 7508. DOI: 10.1038/ncomms8508

[59] C-H Activation Generates Period-Shortening Molecules That Target Cryptochrome in the Mammalian Circadian Clock

Tsuyoshi Oshima, Iori Yamanaka, Anupriya Kumar, Junichiro Yamaguchi, Taeko Nishiwaki-Ohkawa, Kei Muto, Rika Kawamura, Tsuyoshi Hirota,  Kazuhiro Yagita,  Stephan Irle, Steve A. Kay, Takashi Yoshimura and Kenichiro Itami

Angew. Chem., Int. Ed201554, 7193-7197. DOI: 10.1002/anie.201502942 【detail

Highlighted in News Paper (Chu-nichi Shinbun)

[58] Synthesis and characterization of hexaarylbenzenes with five or six different substituents enabled by programmed synthesis

Shin Suzuki, Yasutomo Segawa, Kenichiro Itami and Junichiro Yamaguchi

Nature Chem2015, 7, 227-233. DOI:10.1038/nchem.2174 【detail

[57] Concise Syntheses of Dictyodendrins A and F by a Sequential C–H Functionalization Strategy

Atsushi D. Yamaguchi, Kathryn M. Chepiga, Junichiro Yamaguchi, Kenichiro Itami, and Huw M. L. Davies,

J. Am. Chem. Soc. 2015, ASAP. DOI: 10.1021/ja512059d 【detail

[56] Synthesis, binding affinity and structure–activity relationships of novel, selective and dual targeting CCR2 and CCR5 receptor antagonists

Anna Junker, Artur K. Kokornaczyk, Annelien J. M. Zweemer, Bastian Frehland, Dirk Schepmann, Junichiro Yamaguchi, Kenichiro Itami, Andreas Faust, Sven Hermann, Stefan Wagner, Michael Schäfers,  Michael Koch, Christina Weiss, Laura H. Heitman, Klaus Kopkai and   Bernhard Wünsch

Org. Biomol. Chem.2015, Advance Article DOI: 10.1039/C4OB02397H

[55] Ni-Catalyzed α-Arylation of Esters and Amides with Phenol Derivatives

Eva Koch, Ryosuke Takise, Armido Studer, Junichiro Yamaguchi and Kenichiro Itami

Chem. Commun.201551, 855.  DOI: 10.1039/C4CC08426Hdetail

[54]  Stereodivergent Synthesis of Arylcyclopropylamines by Sequential C–H Borylation and Suzuki–Miyaura Coupling

Shin Miyamura, Misaho Araki, Takayoshi Suzuki, Junichiro Yamaguchi, and Kenichiro Itami

Angew. Chem. Int. Ed. 201554, 846. DOI: 10.1002/anie.201409186

[53]  Key Mechanistic Features of Ni-catalyzed C–H/C–O Biaryl Coupling of Azoles and Naphthalen-2-yl Pivalates

Huiying Xu, Kei Muto, Junichiro Yamaguchi, Cunyuan Zhao, Djamaladdin G Musaev, and Kenichiro Itami

J. Am. Chem. Soc. 2014136, 14834. DOI: 10.1021/ja5071174

[52] β-Selective C–H Arylation of Pyrroles Leading to Concise Syntheses of Lamellarins C and I

Kirika Ueda , Kazuma Amaike , Richard M. Maceiczyk , Kenichiro Itami , and Junichiro Yamaguchi

J. Am. Chem. Soc. 2014136, 13226. DOI: 10.1021/ja508449y 【detail

Most Read Article (September, 2014) 

[51]  Regioselective Allylic C–H Oxidation of Terminal Alkenes with Pd/sulfoxide-oxazoline Catalyst

Hiroki Kondo, Feng Yu, Junichiro Yamaguchi, Guosheng Liu, and Kenichiro Itami

Org. Lett201416, 4212. DOI: 10.1021/ol5019135 【detail

[50] Nickel-Catalyzed α-Arylation of Ketones with Phenol Derivatives

Ryosuke Takise, Kei Muto, Junichiro Yamaguchi and Kenichiro Itami

Angew. Chem. Int. Ed201453, 6791. DOI: 10.1002/anie.201403823

[48]  Manganese-Catalyzed Intermolecular C–H/C–H Coupling of Carbonyls and Heteroarenes

Keika Hattori, Asraa Ziadi, Kenichiro Itami, and Junichiro Yamaguchi

Chem. Commun. 2014, 50, 4105. DOI:10.1039/C4CC01376J 【detail

Most Read Article (March, 2014) 

[47] Late-Stage C–H Coupling Enables Rapid Identification of HDAC Inhibitors: Synthesis and Evaluation of NCH-31 Analogues

Hiromi Sekizawa, Kazuma Amaike, Yukihiro Itoh,  Takayoshi Suzuki, Kenichiro Itami, and Junichiro Yamaguchi

ACS. Med. Chem. Lett2014, Just Accepted Manuscript. DOI: 10.1021/ml500024s 【detail

[46]  Diverse Modification of the 4-Methylphenyl Moiety of TAK-779 by Late-Stage Suzuki-Miyaura Cross-Coupling

Anna Junker, Dirk Schepmann, Junichiro Yamaguchi, Kenichiro Itami, Andreas Faust, Klaus Kopka, Stefan Wagner, Bernhard Wünsch

Org. Biomol. Chem. 201412, 177-186. DOI: 10.1039/C3OB41873A

[45] Programmed Synthesis of Arylthiazoles through Sequential C-H Couplings

Satoshi Tani, Takahiro N. Uehara, Junichiro Yamaguchi and Kenichiro Itami,

Chem. Sci. 2014, 5, 123-125. DOI: 10.1039/C3SC52199K 【detail

Most Read Articles in October in 2013

[44]  Isolation, Structure, and Reactivity of an Arylnickel(II) Pivalate Complex in Catalytic C-H/C-O Biaryl Coupling

Kei Muto, Junichiro Yamaguchi, Aiwen Lei, and Kenichiro Itami

J. Am. Chem. Soc. 2013, 135, 16384–16387. DOI: 10.1021/ja409803xdetail

[43] Palladium-Catalyzed C–H and C–N Arylation of Aminothiazoles with Arylboronic Acids

Takahiro N. Uehara, Junichiro Yamaguchi, Kenichiro Itami

Asian J. Org. Chem. 20132, 938-942. DOI: 10.1002/ajoc.201300172 【detail

(Dedicated to Professor Teruaki Mukaiyama on the occasion of the 40th anniversary of the Mukaiyama aldol reaction)

Highlighted in Chemistry Views, Highlighted in Synfacts.

[42]  C–H Alkenylation of Azoles with Enols and Esters by Nickel Catalysis

Lingkui Meng, Yuko Kamada, Kei Muto, Junichiro Yamaguchi, and Kenichiro Itami

Angew. Chem. Int. Ed. 2013, 52, 10048 DOI: 10.1002/anie.201304492 【detail

[41] Aromatic C–H Coupling with Hindered Arylboronic Acids by Pd/Fe Dual Catalysts

Kazuya Yamaguchi, Hiroki Kondo, Junichiro Yamaguchi, and Kenichiro Itami

Chem. Sci. 2013, 4, 3753-3757. DOI: 10.1039/C3SC51206A 【detail

Most Read Articles in June in 2013

[40] Synthesis of Thiophene-Based TAK-779 Analogues by C–H Arylation

Anna Junker, Junichiro Yamaguchi, Kenichiro Itami, and Bernhard Wünsch

J. Org. Chem. 201378, 5579–5586. DOI: 10.1021/jo400692p 【detail

[39] Nickel-Catalyzed Direct Coupling of Heteroarenes

Junichiro Yamaguchi, Kei Muto, Kazuma Amaike, Takuya Yamamoto, and Kenichiro Itami

J. Synth. Org. Chem. Jpn. 201371, 576–583.

[38] Improvement of σ1 receptor affinity by late-stage C–H bond arylation of spiro cyclic lactones

Christina Meyer, Benedikt Neue, Dirk Schepmann, Shuichi Yanagisawa, Junichiro Yamaguchi, Ernst-Ulrich Würthwein, Kenichiro Itami, Bernhard Wünsch,

BioorgMed. Chem.  2013, 21, 1844. DOI: 10.1016/j.bmc.2013.01.038

[37]  Pd-catalyzed direct C-H bond functionalization of spirocyclic sigma-1 ligands: generation of a pharmacophore model and analysis of reverse binding mode by docking into a 3D homology model of the sigma-1 receptor

Christina Meyer, Dirk Schepmann, Shuichi Yanagisawa, Junichiro Yamaguchi, Valentina Dal Col, Erik Laurini, Kenichiro Itami, Sabrina Pricl, and Bernhard Wünsch

J. Med. Chem. 201255, 8047. DOI: 10.1021/jm300894h 【detail

[36] Decarbonylative C–H Coupling of Azoles and Aryl Esters: Unprecedented Nickel Catalysis and Application to the Synthesis of Muscoride A

Kazuma Amaike, Kei Muto, Junichiro Yamaguchi, and Kenichiro Itami,

J. Am. Chem. Soc. 2012134, 13573–13576. DOI: 10.1021/ja306062c 【detail

Highlighted in Newspapers (Chu-nichiAsahi, The Chemical Daily, Yahoo!News, Mynavi-News, Nikkan kogyoKagaku Shinbun)

Most Read Articles in August 2012

[35] Late-Stage C–H Bond Arylation of Spirocyclic sigma-1 Ligands for Analysis of Complementary sigma-1 Receptor Surface

Christina Meyer, Dirk Schepmann, Shuichi Yanagisawa, Junichiro Yamaguchi, Bernhard Wünsch, and Kenichiro Itami

Eur. J. Org. Chem. 2012, 5972–5979. DOI: 10.1002/ejoc.201200837 【detail

[34] Pd- and Cu-catalyzed C–H Arylation of Indazoles

Keika Hattori, Kazuya Yamaguchi, and Kenichiro Itami

Tetrahedron (Special Issue)201268, 7605-7612.  DOI: 10.1016/j.tet.2012.05.091

[33] Hindered Biaryls by C-H Coupling: Bisoxazoline-Pd Catalysis Leading to Enantioselective C-H Coupling

Kazuya Yamaguchi, Junichiro Yamaguchi, Armido Studer, and Kenichiro Itami

Chem. Sci, 2012, 7, 1256. DOI:10.1039/C2SC20277Hdetails

Highlighted RSC Chemical Science blog, Most Read Articles in March and April 2012

 

Assistant Professor (with Kenichiro Itami)

[32] Mechanistic Studies on the Pd-catalyzed Direct C¿H Arylation of 2-Substituted Thiophene Derivatives with Arylpalladium Bipyridyl Complexes

Marc Steinmetz, Kirika Ueda, Stefan Grimme, Junichiro Yamaguchi, Sylvia Kirchberg, Kenichiro Itami, Armido Studer

Chem. Asian J. 20127, 1256–1260. DOI: 10.1002/asia.201101011 【details

[31] Nickel-Catalyzed C−H/C−O Coupling of Azoles with Phenol Derivatives

J. Am. Chem. Soc. 2012134, 169-172. DOI: 10.1021/ja210249h 【details

Highlighted in Newspapers (YomiuriChu-nichiThe Chemical DailyYahoo!News, NanotechJapan Nikkan kogyoKagaku Shinbun), Most Read Articles (January, 2012) 

[30] Synthesis of Dragmacidin D via Direct C-H Couplings

Debashis, Mandal, Atsushi, D. Yamaguchi,  Junichiro, Yamaguchi,  Kenichiro Itami, J. Am. Chem. Soc. 2011133, 19660–19663. DOI: 10.1021/ja209945x 【details

Most Read Articles (November 2011), Highlighted in Chemistry World  

[29] Exploitation of an additional hydrophobic pocket of σ1 receptors: Late-stage diverse modifications of spirocyclic thiophenes by C–H bond functionalization

C. Meyer, B. Neue, D. Schepmann, S. Yanagisawa, J. Yamaguchi, E.-U. Würthwein, K. Itami, B. Wünsch

Org. Biomol. Chem2011, 2011, 9, 8016. DOI: 10.1039/C1OB06149F

[28] Nickel-Catalyzed C–H Arylation of Azoles with Haloarenes: Scope, Mechanism, and Applications to the Synthesis of Bioactive Molecules

T. Yamamoto, K. Muto, M. Komiyama, J. Canivet, J. Yamaguchi, and K. Itami Chem. Eur. J. 2011, Early View. DOI: 10.1002/chem.201101091. 【details

Highlighted in SYNFACTS

[27] Oxidative C–H/C–H Coupling of Azine and Indole/Pyrrole Nuclei: Palladium Catalysis and Synthesis of Eudistomin U

A. D. Yamaguchi, D. Mandal, J. Yamaguchi, and K. Itami, Chem. Lett. 2011, 40, 555 -557. DOI: 10.1246/cl.2011.555 details

Selected as “Editor’s Choice” Most-Accessed Articles, Highlighted in Angew. Chem. Int. Ed.

[26] Oxidative Biaryl Coupling of Thiophenes and Thiazoles with Arylboronic Acids through Palladium Catalysis: Otherwise-Difficult C4-Selective C-H Arylation Enabled by Boronic Acids

S. Kirchberg, S. Tani, K. Ueda, J. Yamaguchi, A. Studer, and K. Itami, Angew. Chem. Int. Ed. 2011, 50, 2387.

DOI: 10.1002/anie.201007232details

Highlighted in SYNFACTS

[25] A General Catalyst for the β-Selective C-H Bond Arylation of Thiophenes with Iodoarenes

Kirika Ueda, Shuichi Yanagisawa, Junichiro Yamaguchi, and Kenichiro Itami, Angew. Chem. Int. Ed. 2010, 49,8946.

DOI; 10.1002/anie.201005082

Highlighted in SYNFACTS

[24]Fe-Catalyzed Oxidative Coupling of Heteroarenes and Methylamines

M. Ohta, M. P. Quick, J. Yamaguchi, B. Wünsch, and K. Itami Chem. Asian J. 2009, 4, 1416.

DOI:10.1002/asia.200900157

Most-Accessed Articles (July 2009)

[23] Nickel-Catalyzed Biaryl Coupling of Heteroarenes and Aryl Halides/Triflates

J. Canivet, J. Yamaguchi, I. Ban, K. Itami, Org. Lett., 2009, 11, 1733.

DOI: 10.1021/ol9001587

Highlighted in SYNFACTS

Postdoctoral (with Phil. S. Baran)

[22] Enantioselective Total Syntheses of (−)-Palau’amine, (−)-Axinellamines, and (−)-Massadines

I. B. Seiple, S. Su, I. S. Young, A. Nakamura, J. Yamaguchi, L. Jørgensen, R. A. Rodriguez, D. P. O’Malley, T. Gaich, M. Kck, and P. S. BaranJ. Am. Chem. Soc. 2011, ASAP. DOI: 10.1021/ja2047232

[21] Total Synthesis of Palau’amine

I. B. Seiple, S. Su, I. S. Young , C. A. Lewis , J Yamaguchi,  P. S. Baran Angew. Chem. Int. Ed. 2010, 49, 1095.

DOI: 10.1002/anie.200907112

Selected as VIP paper and Cover Picture in Angew. Chem. Int. Ed.

Highlighted in NatureC&ENWired Science,SciencedailyR&DHealth Candal.com, Chemistry World Blog(RSC)Tot. Syn. Dot ComChem-StationC2W – C2W

Financial ExpressAngew. Chem., Gendai-Kagaku

Most-Accessed Articles (January 2010, 6/2009~7/2010)

[20] Total Synthesis of (±)-Axinellamines A and B

D. P. O’Malley, J. Yamaguchi, I. S. Young, I. B. Seiple, P. S. BaranAngew. Chem. Int. Ed., 2008, 47, 3581.

DOI: 10.1002/anie.200801138

Selected as VIP paper and Inside Cover in Angew. Chem. Int. Ed.

Highlighted in Tot. Syn. Dot Com

[19] Synthesis of 1,9-Dideoxy-pre-axinellamine

J. Yamaguchi, I. B. Seiple, I. S. Young, D. P. O’Malley, M. Maue, P. S. BaranAngew. Chem. Int. Ed., 2008, 47, 3578.

DOI: 10.1002/anie.200705913

Visiting graduate student (Prof. K. C. Nicolaou)

[18]Total Synthesis of Marinomycins A-C and of Their Monomeric Counterparts Monomarinomycin A and iso-Monomarinomycin A

K. C. Nicolaou, A. L. Nold, R. R. Milburn, C. S. Schindler, K. P. Cole, J. Yamaguchi, J. Am. Chem. Soc., 2007129, 1760.

DOI: 10.1021/ja068053p

Graduate school (with Prof. Yujiro Hayashi)

[17] The Asymmetric Total Synthesis of (+)-Cytotrienin A, an Ansamycin-Type Anticancer Drug

Y. Hayashi, M. Shoji, H. Ishikawa, J. Yamaguchi, T. Tamura, H. Imai, Y. Nishigaya, K. Takabe, H. Kakeya, H. Osada, Angew. Chem. Int. Ed., 200847, 6657.

DOI: 10.1002/anie.200802079

Highlighted in SYNFACTS

[16] Direct Asymmetric a-Amination of Cyclic Ketones Catalyzed by Siloxyproline

Y. Hayashi, S. Aratake, Y. Imai, K. Hibino, Q. -Y. Chen, J. Yamaguchi, T. Uchimaru, Chem. Asian J., 2008, 3, 225.

DOI: 10.1002/asia.200700307

[15] Organocatalyst-Mediated Enantioselective Intramolecular Aldol Reaction Featuring the Rare Combination of Aldehyde as Nucleophile and Ketone as Electrophile

Y. Hayashi, H. Sekizawa, J. Yamaguchi, H. Gotoh, J. Org. Chem., 2007, 72, 6493.

DOI: 10.1021/jo0709100

[14] Enantio- and Diastereoselective Total Synthesis of (+)-Panepophenanthrin, a Ubiquitin-Activating Enzyme Inhibitor, and Biological Properties of Its New Derivatives

M. Matsuzawa, H. Kakeya, J. Yamaguchi, M. Shoji, R. Onose, H. Osada, Y. Hayashi, Chem. Asian J., 2006, 1, 845.

DOI: 10.1002/asia.200600199

[13] Large Nonlinear Effect Observed in the Enantiomeric Excess of Proline in Solution and That in the Solid State

Y. Hayashi, M. Matsuzawa, J. Yamaguchi, S. Yonehara, Y. Matsumoto, M. Shoji, D. Hashizume, H. Koshino, Angew. Chem. Int. Ed., 2006, 45, 4593.

DOI: 10.1002/anie.200601506

[12] Concise Enantio- and Diastereoselective Total Syntheses of Fumagillol, RK-805, FR65814, Ovalicin, and 5-Demethylovalicin

J. Yamaguchi, M. Toyoshima, M. Shoji, H. Kakeya, H. Osada, Y. Hayashi, Angew. Chem. Int. Ed., 2006, 45, 789.

DOI: 10.1002/anie.200502826

[11] Determination by Asymmetric Total Synthesis of The Absolute Configuration of Lucilactaene, a Cell Cycle Inhibitor in p53-Transfected Cells

J. Yamaguchi, H. Kakeya, T. Uno, M. Shoji, H. Osada, Y. Hayashi, Angew. Chem. Int. Ed., 2005, 44, 3110.

DOI: 10.1002/anie.200500060

[10] A Highly Active 4-Siloxyproline Catalyst for Asymmetric Synthesis

Y. Hayashi, J. Yamaguchi, K. Hibino, T. Sumiya, T. Urushima, M. Shoji, D. Hashizume, H. Koshino, Adv. Synth. Catal., 2004, 346, 1435.

DOI: 10.1002/adsc.200404166

Highlighted in Letters in Organic Chemistry, 2005, 2, 5 , 392-397 (News and Views).

[9] Structure-Activity Relationships of Epolactaene Derivatives: Structural Requirements for Inhibition of Hsp60 Chaperone Activity

Y. Nagumo, H. Kakeya, J. Yamaguchi, T. Uno, M. Shoji, Y. Hayashi, H. OsadaBioorg. Med. Chem. Lett., 2004, 14, 4425.

DOI: 10.1016/j.bmcl.2004.06.054

[8] Direct Proline-Catalyzed Asymmetric a-Aminoxylation of Aldehydes and Ketones

Y. Hayashi, J. Yamaguchi, T. Sumiya, K. Hibino, M. Shoji, J. Org. Chem., 2004, 69, 5966-5973.

DOI: 10.1021/jo049338s

[7] Direct Proline-Catalyzed Asymmetric a-Aminoxylation of Ketones

Y. Hayashi, J. Yamaguchi, T. Sumiya, M. Shoji, Angew. Chem. Int Ed., 2004, 43, 1112.

DOI: 10.1002/ange.200353085

Selected as VIP paper in Angew. Chem. Int. Ed.

[6] Direct Proline Catalyzed Asymmetric a-Aminooxylation of Aldehydes

Y. Hayashi, J. Yamaguchi, K. Hibino, M. Shoji, Tetrahedron Lett., 2003, 44, 8293.

DOI: 10.1016/j.tetlet.2003.09.057

[5] Asymmetric Total Synthesis of Pseurotin A

Y. Hayashi, M. Shoji, S. Yamaguchi, T. Mukaiyama, J. Yamaguchi, H. Kakeya, H. OsadaOrg. Lett., 2003, 5, 2287.

DOI:10.1021/ol034630s

[4] Asymmetric Total Synthesis of (-)-Azaspirene, a Novel Angiogenesis Inhibitor

Y. Hayashi, M. Shoji, J. Yamaguchi, K. Sato, S. Yamaguchi, T. Mukaiyama, K. Sakai, Y. Asami, H. Kakeya, H. Osada, J. Am. Chem. Soc., 2002, 124, 12078.

DOI: 10.1021/ja0276826

[3] The Diastereoelective Asymmetric Total Synthesis of NG-391, a Neuronal Cell-Protecting Molecule

Y. Hayashi, J. Yamaguchi, M. Shoji, Tetrahedron, 2002, 58, 9839.

DOI: 10.1016/S0040-4020(02)01290-5

[2] Diastereoselective Total Synthesis of Both Enantiomers of Epolactaene

Y. Hayashi, J. Kanayama, J. Yamaguchi, M. Shoji, J. Org. Chem., 2002, 67, 9443.

DOI:10.1021/jo025641m

[1] Total Synthesis of (+)-Epoxyquinols A and B

M. Shoji, J. Yamaguchi, H. Kakeya, H. Osada, Y. Hayashi, Angew. Chem. Int. Ed., 2002, 41, 3192.

DOI:10.1002/1521-3773(20020902)41:17%3C3192::AID-ANIE3192%3E3.0.CO;2-E

Selected as Hot paper in Angew. Chem. Int. Ed.

Accounts and Review

 

[7] Synthesis of Bioactive Compounds through C-H Bond Functionalization

Junichiro Yamaguchi and Kenichiro Itami

Fine Chemicals 2012, 41, 38.

[6] Recent Progress in Nickel-Catalyzed Biaryl Coupling

Junichiro Yamaguchi, Kei Muto, and Kenichiro Itami

Eur. J. Org. Chem. 2012, Early View. DOI: 10.1002/ejoc.201200914 【detail

[5] C-H Bond Functionalization: Emerging Synthetic Tools for Natural Products and Pharmaceuticals

Junichiro Yamaguchi, Atsushi D. Yamaguchi, and Kenichiro Itami

Angew. Chem. Int. Ed. 201251, 8960–9009.  10.1002/anie.201201666 【detail

Selected as the Cover of the Issue.
Highlighted in Chemistry Views.

[4] Synthesis of Bioactive Compounds through C-H Bond Functionalization (Japanese)

J. Yamaguchi, K. Itami, Catalysts & Catalysis, 2011, 53, 293.  Link

Most-Accessed Articles

[3] Syntheses of Fumagillin and ovalicin

J,Yamaguchi, Y. Hayashi, Chem. Eur. J., 2010, 16, 3884.

DOI: 10.1002/chem.200902433

[2] Baran Lab in the Scripps research institute

J. Yamaguchi, Organomet News, 2009, 16.

[1]. Asymmetric Total Synthesis of a Natural Product Using Catalytic Enantioselective Stereoablative Reactions

J. Yamaguchi, J. Synth. Org. Chem., Jpn 2009, 67, 166.

 

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