Publications-Junichiro Yamaguchi-

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Publications-Junichiro Yamaguchi-

Publications-Junichiro Yamaguchi-

【発表論文】

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

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

Nature. Commun. 2015, 6, 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. Ed. 2015, 54, 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 Chem. 2015, 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., 2015, 51, 855. DOI: 10.1039/C4CC08426H【detail】

[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. 2015, 54, 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. 2014, 136, 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. 2014, 136, 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. Lett. 2014, 16, 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. Ed. 2014, 53, 6791. DOI: 10.1002/anie.201403823

[49] 2,4- and 2,5-Disubstituted Arylthiazoles: Rapid Synthesis by C–H Coupling and Biological Evaluation

Lilia Lohrey, Takahiro N. Uehara, Satoshi Tani, Junichiro Yamaguchi, Hans-Ulrich Humpf and Kenichiro Itami

Eur. J. Org. Chem. 2014, 3387. DOI: 10.1002/ejoc.201402129 【detail】

[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. Lett. 2014, 582. DOI: 10.1021/ml500024s 【detail】

Most Read Article (March, 2014)

[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. 2014, 12, 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, Highlighted in Synfacts

[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/ja409803x【detail】

[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. 2013, 2, 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. 2013, 78, 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. 2013, 71, 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,

Bioorg. Med. 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. 2012, 55, 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. 2012, 134, 13573–13576.

DOI: 10.1021/ja306062c　【detail】

Highlighted in Newspapers (Chu-nichi, Asahi, The Chemical Daily, Yahoo!News, Mynavi-News, Nikkan kogyo, Kagaku 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), 2012, 68, 7605-7612.

DOI: 10.1016/j.tet.2012.05.091 【detail】

[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/C2SC20277H【details】

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

[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. 2012, 7, 1256–1260.

DOI: 10.1002/asia.201101011 【detail】

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

Kei Muto, Junichiro Yamaguchi, Kenichiro Itami,

J. Am. Chem. Soc. 2012, 134, 169-172.

DOI: 10.1021/ja210249h 【details】

Highlighted in Newspapers (Yomiuri, Chu-nichi, The Chemical Daily, Yahoo!News, NanotechJapan Nikkan kogyo, Kagaku Shinbun), Most Read Articles (January, 2012), Highlighted as a “SynStory” article in SYNFORM (April 2012), Highlighted in Chemical Engineering (Feb 2012)

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

Debashis Mandal, Atsushi D. Yamaguchi, Junichiro Yamaguchi, Kenichiro Itami, J. Am. Chem. Soc. 2011, 133, 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. Chem. 2011, 9, 8016.

DOI: 10.1039/C1OB06149F

[28] 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. Baran, J. Am. Chem. Soc. 2011, 133, 14710.

DOI: 10.1021/ja2047232

Most Read Articles (October 2011)

[27] 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, 17, 10113.

DOI: 10.1002/chem.201101091. 【details】

Highlighted in SYNFACTS

[26] 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.

[25] 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.201007232 【details】

Highlighted in SYNFACTS

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

K. Ueda, S. Yanagisawa, J. Yamaguchi, K. Itami, Angew. Chem. Int. Ed. 2010, 49, 8946.

DOI; 10.1002/anie.201005082 【details】

Highlighted in SYNFACTS

[23] 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 Nature, C&EN, Wired Science,Sciencedaily, R&D, Health Candal.com, Chemistry World Blog(RSC), Tot. Syn. Dot Com, Chem-Station, C2W – C2W

Financial Express, Angew. Chem., Gendai-Kagaku

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

[22]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 【details】
Most-Accessed Articles (July 2009)

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

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

DOI: 10.1021/ol9001587

Highlighted in SYNFACTS

Top 20 Most Cited Articles 2009-2011
[20] 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., 2008, 47, 6657.

DOI: 10.1002/anie.200802079
Highlighted in SYNFACTS

[19] Total Synthesis of (±)-Axinellamines A and B
D. P. O’Malley, J. Yamaguchi, I. S. Young, I. B. Seiple, P. S. Baran, Angew. 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

[18] Synthesis of 1,9-Dideoxy-pre-axinellamine
J. Yamaguchi, I. B. Seiple, I. S. Young, D. P. O’Malley, M. Maue, P. S. Baran, Angew. Chem. Int. Ed., 2008, 47, 3578.

DOI: 10.1002/anie.200705913
[17] 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
[16] 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
[15]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., 2007, 129, 1760.

DOI: 10.1021/ja068053p
[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. Osada, Bioorg. 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. Osada, Org. 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.

【総説、解説記事】

[9] Nickel-Catalyzed Direct Coupling of Heteroarenes

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

J. Synth. Org. Chem. Jpn. 2013, 71, 576. DOI:10.5059/yukigoseikyokaishi.71.576

[8] Decarbonylative C–H Biaryl Coupling (Japanese)

Junichiro Yamaguchi and Kenichiro Itami

Kagaku 2013, 68, 35. [Link]

[7] Recent Progress in Nickel-Catalyzed Biaryl Coupling

Junichiro Yamaguchi, Kei Muto, and Kenichiro Itami

Eur. J. Org. Chem. 2013, 19–30. DOI: 10.1002/ejoc.201200914 【detail】