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Researcher Information

last modified:2020/01/22

Vice President MUKAI Chisato

Mail

Faculty, Affiliation

Administration Office

College and School Educational Field


Division of Natural System, Graduate School of Natural Science and Technology
School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences
School of Pharmacy, College of Medical, Pharmaceutical and Health Sciences

Laboratory

Pharmaceutical and Organic Chemistry TEL:076-234-4411 FAX:076-234-4410

Academic Background

【Academic background(Doctoral/Master's Degree)】
Osaka University Doctor 1981 Completed
【Academic background(Bachelor's Degree)】
Kanazawa University 1976

Career

Kanazawa University

Year & Month of Birth

1953/06

Academic Society


American Chemical Society

Award




○Takeda Scientific Foundation(1993/05/01)
○The Research Foundation for Pharmaceutical Sciences(1994/03/25)
○Outstanding Contribution Award Graduate School of Natural Science & Technology, Kanazawa University(2008/03/25)
○Outstanding Contribution Award Graduate School of Natural Science & Technology, Kanazawa University(2008/03/25)
○Outstanding Contribution Award Graduate School of Natural Science & Technology, Kanazawa University(2009/03/25)

Specialities

Chemical pharmacy、Drug development chemistry

Speciality Keywords

organometallic chemistry, synthetic organic chemistry, natural product chemistry

Research Themes

Development of Highly Stereoselective Reactions Based on Organometallics and Their Application to Syntheses of Biologically Active Compound

There are two major programs are going on in my laboratory. The first topic involves development of novel reactions based on transition metals such as cobalt and rhodium. In particular, recent our interests focus on the novel ring-closing reactions between allene and other unsaturated bonds such as alkene and alkyne by taking advantage of the characteristic feature of the former. The second one is studies on total syntheses of complex natural products using the newly developed ring-closing reactions as mentioned above in a highly efficient manner.

Books

  •  R. Ukon, N. Kuroda A New Entry to Carbocycles: Synthesis of Cyclopentene and Cyclohexene Derivatives Through Endo-mode Ring Closure of Allenyl Sulfones. 44  1583-1586 2003/03
  •  T. Koazaka, S. Suzuki, I. J. Kim New Entry to the Pauson-Khand Reaction: Trimethylgermyl Group at the Triple Bond Terminus as a Laten Functional Group. 60  2497-2507 2004/07
  •  I. Nomura Studies on The Total Synthesis of Streptazolin and Its Related Natural Products: First Total Synthesis of 8a-Hydroxystreptazolone. 2004/07
  •  M. Kobayashi, S. Kubota, Y. Takahashi, S. Kitagaki Construction of Azacycles Based on Endo-Mode Cyclization of Allenes. 69  2128-2136 2004/09
  •  F. Inagaki, T. Yoshida, S. Kitagaki Rh(I)-Catalyzed Ring-Closing Reaction of Allenynes: Selective Construction of Cycloheptene, Bicyclo[5.3.0]decadienone, and Bicyclo[5.2.0]nonene Frameworks. 45  4117-4121 2004/08

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  •  S.Kitagaki,K.Ohdachi,K.Katoh, Sequential Pericyclic Reaction of Ene-diallenes: An Efficient Approach to the Steroid Skeleton. 8  95-98 2006/02
  •  M. Ohta, H. Yamashita, S. Kitagaki Base-Catalyzed Endo-Mode Cyclization: Easy Preparation of Five- to Nine-Membered Oxacycles. 69  6867-6873 2004/09
  •  N. Miyakoshi, D. Aburano Total Syntheses of Naturally Occurring Diacetylenic Spiroacetal Enol Ethers. 70  6045-6052 2005/04
  •  N. Kuroda, R. Ukon, R. Itoh Preparation of Carbocycles via Base-Catalyzed Endo-Mode Cyclization of Allenes. 70  6282-6290 2005/05
  •  F. Inagaki, T. Yoshida, K. Yoshitani, Y. Hara, S. Kitagaki Rh(I)-Catalyzed Pauson-Khand Reaction and Cycloisomerization of Allenes: Selective Preparation of Monocyclic, Bicyclo[m.3.0], and Bicyclo[5.2.0] Ring Systems. 70  7159-7171 2005/06
  •  T. Hirose, S. Teramoto, S. Kitagaki Rh(I)-catalyzed Allenic Pauson-Khand Reaction: First Construction of the Bicyclo[6.3.0]undecadienone Ring System. 61  10983-10994 2005/07
  •  Y. Takahashi A New Entry to the Synthesis of 2,3-Disubstituted Indoles. 7  5793-5796 2005/08
  •  S. Kitagaki, Y. Okumura Synthesis of Naphtho[b]cyclobutenes from 1,2-Bis(3-propynol)benzenes. 47  1849-1852 2006/03
  •  F. Inagaki Rhodium(I)-Catalyzed Intramolecular Pauson-Khand-Type [2+2+1] Cycloaddition of Allenenes. 8  1217-1220 2006/04
  •  N. Kuroda, Y. Takahashi, K. Yoshinaga A Novel Generation of Indole-2,3-quinodimethanes. 8  1843-1845 2006/05
  •  R. Itoh Grubbs Catalyst-Mediated Cycloisomerization of Allenenes. 47  3971-3974 2006/06
  •  S. Kitagaki, K. Katoh, K. Ohdachi, Y. Takahashi, D. Shibata Intermolecular [4+2] Cycloaddition of o-Quinodimethanes Derived from Ene-bis(sulfinylallenes). 71  6908-6914 2006/07
  •  S. Kitagaki, Y. Okumura Reaction of Ene-bis(phosphinylallenes): [2+2] versus [4+2] Cycloaddition. 62  10311-19320 2006/10
  •  S. Kitagaki, D. Shibata Studies of Ring-Closing Mode of 4-Hydroxy-2-vinylindenebutanoates: 5-Exo-Trig versus 5-Endo-Dig. 48  1735-1738 2007/01
  •  F. Inagaki, T. Kawamura Rh(I)-catalyzed Pauson-Khand Reaction of 1-Phenylsulfonyl-1,2-octadien-7-yne Derivatives. 63  5154-5160 2007/03
  •  Y. Hara, Y. Miyashita, F. Inagaki Thermal [2+2] Cycloaddition of Allenynes: Easy Construction of Bicyclo[6.2.0]deca-1,8-dienes, Bicyclo[5.2.0]nona-1,7-dienes, and Bicyclo[4.2.0]octa-1,6-dienes. 72  4454-4461 2007/04
  •  S. Kitagaki, S. Teramoto Ring-closing Reaction of Allenic/propargylic Anions Generated by Base Treatment of Sulfonylallenes. 9  2549-2552 2007/05
  •  D. Aburano, T. Yoshida, N. Miyakoshi Synthesis of Hexahydropyrrolo[2,3-b]indole Alkaloids Based on the Aza-Pauson-Khand-Type Reaction of Alkynecarbodiimides. 72  6878-6884 2007/08
  •  T. Kozaka, N. Miyakoshi Stereoselective Total Syntheses of Three Lycopodium Alkaloids, (-)-Magellanine, (+)-Magellaninone, and (+)-Paniculatine Based on Two Pauson-Khand Reactions. 72  10147-10154 2007/12
  •  T. Hirose, N. Miyakoshi Total Synthesis of (+)-Achalensolide Based on the Rh(I)-Catalyzed Allenic Pauson-Khand-Type-Reaction. 73  1061-1066 2008/01
  •  Y. Hayashi, N. Miyakoshi, S. Kitagaki Stereoselective Total Syntheses of Uncommon Sesquiterpenoids from Jatropha neopauciflora. 10  2385-2388 2008/03
  •  N. Miyakoshi, Y. Ohgaki, K. Masui Synthesis of(±)-Lauthisan. 74  185-189 2007/10
  •  H. Hakuba, S. Kitagaki Sequential Pericyclic Reaction of Ene-diallene: Synthesis of (±)-Estrone 63  12639-12645 2007/09
  •  T. Yoshida, M. Sorimachi, A. Odani Co2(CO)8-Catalyzed Intramolecular Hetero-Pauson-Khand Reaction of Alkynecarbodiimide: Synthesis of (±)-Physostigmine. 8  83-86 2006/01

Papers

  •  Enantioselective Total Synthesis of (+)-Sieboldine A M. K. Abd El-Gaber, S. Yasuda, E. Iida, C. Mukai. Org. Lett. 19 320-323  2017/01
  •  RhI-Catalyzed Cycloaddition between Allenyl -Bonds and C-C Triple Bonds C. Mukai, S. Yasuda. J. Synth. Org. Chem. Jpn. 174 1108-1118  2016/12
  •  The discovery of 2,5-isomers of triazole-pyrrolopyrimidine as selective Janus kinase 2 (JAK2) inhibitors versus JAK1 and JAK3 S.Lee, K. B. Yoon, H. J. Lee, J. Kim, Y. K. Chung. W. Cho, C. Mukai, S. Choi, K. W. Kang, S. Han, H. Ko, Y. Kim Bioorg. Med. Chem. 24 5036-5046  2016/08
  •  Planar chiral [2.2]paracyclophane-based phosphine-phenol catalysts: application to the aza-Morita-Baylis-Hillman reaction of N-sulfonated imines with various vinyl ketones N. Takenaga, S. Adachi, A. Furusawa, K. Nakamura, N. Suzuki, Y. Ohta, M. Komizu, C. Mukai, S. Kitagaki. Tetrahedron 72 6892-6897  2016/09
  •  Construction of Hexahydrophenanthrenes By Rhodium(I)-Catalyzed Cycloisomerization of Benzylallene-Substituted Internal Alkynes through C-H Activation Y. Kawaguchi, S. Yasuda, C. Mukai.  Angew. Chem. Int. Ed.  55 10473-10477  2016/07

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  •  Chemo- and Regioselective Rhodium(I)-Catalyzed [2+2+2] Cycloaddition of Allenynes with Alkynes S. Yasuda, Y. Kawaguchi, Y. Okamoto, C. Mukai.  Chem. Eur. J. 22 12181-12188  2016/07
  •  Construction of Azabicyclo[6.4.0]dodecatrienes Based on Rhodium(I)-Catalyzed Intramolecular [6+2] Cycloaddition between Azetidine, Allene, and Alkynes S.Yasuda, H. Yokosawa,C.Mukai. Chem. Pharm, Bull.  64 805-810 2016/03
  •  Energyless CO2 Absorption, Generation, and Fixation Using Atmospheric CO2 F. Inagaki, Y. Okada, C. Matsumoto, M. Yamada, K. Nakazawa, C. Mukai. Chem. Pharm. Bull.  64 8-13 2015/11
  •  Concise Construction of Bicyclo[6.4.0] and -[7.4.0] Frameworks by [4+2] Cycloaddition of 3,4-Dimethylene-2,5-bis(phenylsulfonyl)cycloalk-1-enes C. Mukai, M. Ueda, Y. Takahashi, F. Inagaki Eur. J. Org. Chem. 4412-4422 2015/06
  •   Synthesis of planar chiral [2.2]paracyclophane-based bisoxazoline ligands bearing no central chirality and application to Cu-catalyzed asymmetric O-H insertion reaction  S. Kitagaki, K. Sugisaka, C. Mukai. Org. Biomol. Chem. 13 4833-4836  2015/03
  •  Synthesis of a Carbon Analogue of Scytonemin C. Mukai, K. Arima, S. Hirata, S. Yasuda.  Chem. Pharm. Bull. 63 273-277  2015/01
  •  Air-Stable Cationic Gold(I) Catalyst Featureing a Z-Type Ligand: Promoting Enyne Cyclization F. Ingaki, C. Matsumoto, Y. Okada, N. Maruyama, C. Mukai Angew. Chem. Int. Ed. 54 818-822  2014/12
  •  Rhodium(I)-Catalyzed Cycloisomerization of Allene-Allenylcyclopropanes T. Kawamura, Y. Kawaguchi, K. Sugikubo, F. Inagaki, C. Mukai. Eur. J. Org. Chem. 719-722  2014/11
  •  Stereospecific and Stereoselective Rhodium(I)-Catalyzed Intramolecular [2+2+2] Cycloaddition of Allene-Ene-Ynes: Construction of Bicyclo[4.1.0]heptanes Y. Ohta, S. Yasuda, Y. Yokogawa, K. Kurokawa, C. Mukai. Angew. Chem. Int. Ed.  54 1240-1244  2014/10
  •  Rhodium(I)-Catalyzed Cycloisomerization of Benzylallene-Alkynes through C-H Activation Y. Kawaguchi, S. Yasuda, A. Kaneko, Y. Oura, C. Mukai Angew. Chem. Int. Ed. 53 7608-7612  2014/05
  •  Total synthesis of (+)-kopsihainanine A M. Mizutani, S. Yasuda, C. Mukai CHEMICAL COMMUNICATIONS 50 5782-5785  2014/04
  •  [2+2+1] Cyclization of allenes S. Kitagaki, F. Inagaki, C. Mukai Chem. Soc. Rev. 43 2956-2978 2014/02
  •  Rh(I)-Catalyzed Intramolecular Carbonylative [2+2+1] Cycloaddition Reaction: Preparation of Bicyclo[5.4.0]decadienones with Substituted Cyclopentenone Frameworks C. Mukai, Y. Takahashi, K. Ogawa, Y. Hayashi, F. Inagaki Chem. Pharm. Bull. 62 1 84-87 2013/10
  •  Rhodium(I)-Catalyzed Cycloisomerization of Alkene-Substituted Allenylcyclopropanes: Stereoselective Formation of Bicyclo[4.3.0]nonadienes K. Sugikubo, F. Omachi, Y. Miyanaga, F. Inagaki, C. Matsumoto, C. Mukai Angew. Chem. Int. Ed. 52 43 11369-11372 2013/09
  •  Progress in Carbonylative [2+2+1] Cycloaddition: Utilization of a Nitrile Group as the π Component T. Iwata, F. Inagaki, C. Mukai Angew. Chem. Int. Ed. 52 42 11138-11142 2013/08
  •  Cyclopropanes in Nicholas Reaction: Formation of Spiroketals with a 5-Membered and a 7- or an 8-Membered Ring TETRAHEDRON 69 7659 2013/07
  •  Total Syntheses of (±)-Fawcettimine, (±)-Fawcetidine, (±)-Lycoflexine and (±)-Lycoposerramine-Q CHEMISTRY-A EUROPEAN JOURNAL 19 8665 2013/05
  •  Histidine Augments the Suppression of Hepatic Glucose Production by Central Insulin Action DIABETES 62 2013/05
  •  Characterization and Functionality of Immidazolium Ionic Liquids Modified Magnetic Nanoparticles Y. Li, N. Tang, F. Inagaki, C. Mukai, K. Hayakawa Journal of Chemistry 2013 2013/03
  •  Syntheses of 6-8-5 Tricyclic Ring Systems by Carbonylative [2+2+1] Cycloaddition of Bis(allene)s TETRAHEDRON 69 1509 2013/03
  •  Planar Chiral [2.2]Paracyclophane-Based Bis(thiourea) Catalyst: Application to Asymmetric Henry Reaction CHEMICAL COMMUNICATIONS 49 4030 2013/03
  •  Planar Chiral [2.2]Paracyclophane-Based Phosphine-BrØnsted Acid Catalysts Bearing Exceptionally High Reactivity for Aza-Morita-Baylis-Hillman Reaction TETRAHEDRON LETTERS 54 384 2013/01
  •  Csp3–Csp3 and Csp3–H Bond Activation of 1,1-Disubstituted Cyclopentane JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 134 19580 2012/10
  •  First Total Synthesis of (+)-Indicanone Org. Biomol. Chem. 10 4747 2012/06
  •  Aspergillus niger DLFCC-90 Rhamnoside Hydrolase, a New Type of Flavonoid Glycoside Hydrolase App. Environ. Microbiol. 78 4752 2012/06
  •  Cu-Promoted [2+2] Cycloaddition of 1,4-Bisallenes ORGANIC LETTERS 14 1366 2012/02
  •  Regioselective Intramolecular [3+2] Annulation of Allene-Nitrones CHEMICAL & PHARMACEUTICAL BULLETIN 60 381 2012/01
  •  RhI-Catalyzed [6+2] Cycloaddition of Alkyne-Allenylcyclobutanes: A New Entry for the Synthesis of Bicyclo[6.m.0] Skeletons CHEMISTRY-A EUROPEAN JOURNAL 17 9062 2011/09
  •  A New Procedure for The Preparation of 2-Vinylindoles and Their [4+2] Cycloaddition Reaction TETRAHEDRON 67 5133 2011/06
  •  Can the Crabbé Homologation be Successfully Applied to the Synthesis of 1,3-Disubstituted Allenes? SYNLETT 1129 2011/05
  •  Synthesis of Planar Chiral Pseudo-ortho-Substituted Aryl[2.2]paracyclophanes by Stepwise Successive Palladium-Catalyzed Coupling Reactions TETRAHEDRON-ASYMMETRY 22 986 2011/05
  •  Total Synthesis of (±)-Meloscine ORGANIC LETTERS 13 7 1778 2011/03
  •  Rhodium(I)-Catalyzed Intramolecular Carbonylative [2+2+1] Cycloaddition of Bis(allene)s: Bicyclo[6.3.0]undecadienones and Bicyclo[5.3.0]decadienones fuyuhiko ingaki, shu narita, takuma hasegawa, shinji kitagaki 48 2009/01
  •  Base-Catalyzed Endo-Mode Cyclization: Easy Preparation of Five- to Nine-Membered Oxacycles. JOURNAL OF ORGANIC CHEMISTRY 69 21 6867-6873 2004/10
  •  Efficient Construction of Bicyclo[5.3.0]decenone Skeleton Based on the Rh(I)-Catalyzed Allenic Pauson-Khand Reaction I. Nomura, S. Kitagaki JOURNAL OF ORGANIC CHEMISTRY 68  1376-1385 2003/03
  •  Efficient Construction of Bicyclo[5.3.0]decenone Skeleton Based on the Rh(I)-Catalyzed Allenic Pauson-Khand Reaction. JOURNAL OF ORGANIC CHEMISTRY 68 4 1376-1385 2003/01
  •  Synthesis of Oxaspiro[m.n] Skeletons Based on the Nicholas Reaction TETRAHEDRON 58 12 2755-2762 2002/03
  •  A New Entry to Oxacycles via Base-Catalyzed Endo Mode Cyclization of Allenyl Sulfoxides and Sulfones Org. Lett. 3 21 3385-3387 2001/10
  •  nvestigation of Oxacycle Formation by Base-Promoted Endo-Mode Ring-Closing Reaction of Allenes shinji kitagaki, takamasa kawamura, daisuke shibata TETRAHEDRON 64 2008/03
  •  First Total Synthesis of (-)-Ichthyothereol and Its Acetate J. Org. Chem. 66 17 5875-5880 2001/08
  •  Co2(CO)8-Mediated Endo Mode Cyclization of Epoxy-alcohol: Synthesis of 2-Ethynyl-3-hydroxy-2-methyltetrahydropyran and 2-Ethynyl-3-hydroxy-3-methyltetrahydropyran Derivatives Chem. Pharm. Bull. 49 5 613-618 2001/05
  •  Endo Mode Cyclization of 5,6-Epoxy-7-octyn-1-ol Derivatives J. Org. Chem. 65 20 6761-6765 2000/10
  •  Pauson-Khand Reaction of Optically Active 6,7-Bis(tert-butyldimethylsiloxy)non-1-en-8-ynes J. Org. Chem. 65 20 6654-6659 2000/10
  •  A New Procedure for Construction of Oxocane and Oxonane Derivatives Based on Alkyne-Co2(CO)6 Complex TETRAHEDRON 56 15 2203-2209 2000/04
  •  Studies on Synthesis of Optically Active Twelve-Membered Diynes: A Convergent Construction of a Twelve-Membered Diketodiyne Compound with C2 Symmetry J. Chem. Soc., Perkin Trans. 1 3 737-744 2000/02
  •  Dicobaltoctacarbonyl-Mediated Deoximation Synthesis 11 1872-1874 1999/11
  •  Stereocomplementary Construction of Optically Active Bicyclo[4.3.0]nonenone Derivatives J. Org. Chem. 64 18 6822-6832 1999/08
  •  Revised Structure of Gonioheptolide A Chem. Pharm. Bull. 47 1 131-132 1999/01
  •  A Stereoselective Construction of a Bicyclo[m.n.1] Ring System from Enol-lactones J. Chem. Soc., Perkin Trans. 1 21 3517-3518 1998/10
  •  Total Syntheses of (+)-Secosyrins 1 and 2, and (+)-Syributins 1 and 2 J. Org. Chem. 62 23 8095-8103 1998/10
  •  Diastereocomplementary Construction of Optically Active Bicyclo[4.3.0]nonenone Skeleton Based on Pauson-Khand Reaction TETRAHEDRON LETTERS 39 43 7909-7912 1998/09
  •  Stereoselective Construction of Optically Active Bicyclo[3.3.0]octenone Derivatives Based on Pauson-Khand Reaction J. Chem. Soc., Perkin Trans. 1 17 2903-2915 1998/08
  •  Stereoselective Total Synthesis of (ア)-Swainsonine Based on Endo Mode Cyclization J. Org. Chem. 63 18 6281-6287 1998/08
  •  Stereoselective Syntheses of (+)-Goniotriol, (+)-8-Acetylgoniotriol, (+)-Goniodiol, (+)-9-Deoxygoniopypyrone, (+)-Altholactone, and (-)-Goniofupyrone J. Org. Chem. 62 19 6619-6626 1998/06
  •  A New Procedure for Highly Stereoselective and Regioselective Synthesis of 2-Ethynyl-3-hydroxytetrahydropyran Derivatives Based on Alkyne-Co2(CO)6 Complex TETRAHEDRON 54 5 6 823-850 1998/02
  •  New Glycosylation Reaction Based on Alkyne-Co2(CO)6 Complex TETRAHEDRON LETTERS 38 26 4595-4598 1997/07
  •  First Total Synthesis of (+)-Secosyrin 1 TETRAHEDRON LETTERS 38 14 2511-2512 1997/04
  •  New Approach to AI-77B: Stereoselective Construction of a Potential Precursor of the Amino Acid Side Chain J. Chem. Soc., Perkin Trans. 1 6 913-917 1997/04

Conference Presentations

Arts and Fieldwork

Patent

Theme to the desired joint research

Grant-in-Aid for Scientific Research

○「非プロテイン性シグナル分子を基盤とする新規抗炎症薬の開発」(1997-) 
○「非プロテイン性シグナル分子を基盤とする新規抗炎症薬の開発」(1998-) 
○「エンド型閉環を基盤とする高効率的新規ヘテロ環構築法の開発」(2002-) 
○「アレン化学の新展開」(2004-) 
○「アレンの特性を活用する新規有用反応の開発と天然物合成への応用」(2009-) 
○「アレンと不活性結合を反応成分とする触媒的環化付加反応の開発」(2011-2012) 
○「集積型二重結合を基軸とする環化反応と天然物合成」(2012-2014) 
○「アレンの特性を活用する新規有用反応の開発とその天然物合成への応用研究」(2009-2011) 

Classes (Bachelors)

○Seminar in Organic Chemistry 2(2017)
○Organic Chemistry 2(2017)
○"Community learning ""Super"" Experience Program"(2016)
○Seminar in Organic Chemistry 2(2016)
○Organic Chemistry 2(2016)
○"Community learning ""Super"" Experience Program"(2016)

Classes (Graduate Schools)

○Seminar in Organic Chemistry 2(2016)
○Organic Chemistry 2(2016)

International Project

International Students

Lecture themes

Others (Social Activities)

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