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トップページ >  English >  CV >  Associate Professor Fumihiko Yoshimura, Ph.D.

Associate Professor Fumihiko Yoshimura, Ph.D.


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Fumihiko Yoshimura, Ph.D.

Born 9 March 1974
Current Address

School of Pharmaceutical Sciences
University of Shizuoka
52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan

Phone: 81-54-264-5740
Fax: 81-54-264-5745 (shared)

E-mail: fumi(@)u-shizuoka-ken.ac.jp
Web (Lab.): https://www.us-yakuzo.jp/

RESEARCH FOCUS

• Total synthesis of biologically active natural products with quaternary asymmetric carbon centers
• Development of new reactions
• Molecular design and synthesis of novel molecules with intriguing biological functions

PROFESSIONAL EXPERIENCE

University of Shizuoka, Shizuoka, Japan (May 2017–Present)
• Associate Professor (Laboratory of Professor Toshiyuki Kan)

Hokkaido University, Sapporo, Japan (April 2004−April 2017)
• Assistant Professor, Department of Chemistry, Faculty of Science
(Laboratory of Professors Masaaki Miyashita and Keiji Tanino)

Education

Sloan-Kettering Institute for Cancer Research, New York, NY, USA
(May 2002−March 2004)
• Uehara Memorial Foundation Postdoctoral Fellow
• Research Topic: Total Synthesis of Second-Generation Epothilones and Rishirilide A
Advisor: Professor Samuel J. Danishefsky

Tohoku University, Sendai, Japan (April 1996−March 2002)
• Ph.D. in Organic Chemistry
• Thesis: Synthetic Study of Kedarcidin Chromophore
Research Advisor: Professor Masahiro Hirama

Tohoku University, Sendai, Japan (April 1992−March 1996)
• B.S. degree in Chemistry
Research Advisor: Professor Masahiro Hirama

HONORS AND AWARDS

• Young Chemist Award of the CSJ Hokkaido Branch for 2013 (2014)
• Mitsubishi Tanabe Pharma Award in synthetic Organic Chemistry, Japan (2012)
• Asian Core Program Lectureship Award, 1st International Conference on Cutting-Edge Organic Chemistry in Asia (2006)
• Uehara Memorial Foundation Postdoctoral Fellowship (2002−2004)
• JSPS Research Fellowship for Young Scientist (DC1) (1998−2001)

Publication

RESEARCH PUBLICATIONS (REFEREED)
1. Yoshimura, F.*; Saito, H.; Abe, T.; Tanino, K.*
“Nucleophilic Addition of Alkanenitriles to Aldehydes via In Situ Generated N-Silyl Ketene Imines”
Synlett 2017, 28, in press.

2. Kamada, R.; Kudoh, F.; Yoshimura, F.; Tanino, K.; Sakaguchi, K.*
“Inhibition of Ser/Thr phosphatase PPM1D induces neutrophil differentiation in HL-60 cells”
J. Biochem. 2017, in press.

3. Yoshimura, F.*; Abe, T.; Tanino, K.*
“Synthesis of Aryl Amine Derivatives from Benzyl Nitriles via Electrocyclization of in Situ Generated N-Silyl Ketene Imines”
Org. Lett. 2016, 18, 1630–1633.

4. Ogasawara, S.; Kiyota, Y.; Chuman, Y.; Kowata, A.; Yoshimura, F.; Tanino, K.; Kamada, R.; Sakaguchi, K.*
“Novel Inhibitors Targeting PPM1D Phosphatase Potently Suppress Cancer Cell Proliferation”
Bioorg. Med. Chem. 2015, 23, 6246–6249.

5. Kozakai, Y.; Kamada, R.; Kiyota, Y.; Yoshimura, F.; Tanino, K.; Sakaguchi, K.*
“Inhibition of C-terminal truncated PPM1D enhances the effect of doxorubicin on cell viability in human colorectal carcinoma cell line”
Bioorg. Med. Chem. Lett. 2014, 24, 5593–5596.

6. Yoshimura, F.*; Abe, T.; Tanino, K.*
“Nucleophilic Addition Reactions of Nitriles to Nitrones under Mild Silylation Conditions”
Synlett 2014, 25, 1863–1868.

7. Tanino, K.*; Yamada. T.; Yoshimura, F.; Suzuki, T.*
“Cyanoazulene-based Multistage Redox Systems Prepared from Vinylcyclopropanecarbonitrile and Cyclopentenone via Divinylcyclopropane-rearrangement Approach”
Chem. Lett. 2014, 43, 607–609.

8. Yamada. T.; Yoshimura, F.; Tanino, K.*
“Synthesis of 2-cyano-1,4-cycloheptadiene derivatives via divinylcyclopropane rearrangement and alkylation of novel cycloheptadienyl anion species”
Tetrahedron Lett. 2013, 54, 522–525.

9. Yoshimura, F.*; Kowata, A.; Tanino, K.*
“Stereocontrolled synthesis of carbocyclic compounds with a quaternary carbon atom based on SN2’ alkylation of γ,δ-epoxy-α,β-unsaturated ketones”
Org. Biomol. Chem. 2012, 10, 5431–5442.

10. Yoshimura, F.*; Torizuka, M.; Mori, G.; Tanino, K.*
“Intramolecular Conjugate Addition of α,β-Unsaturated Lactones Having an Alkanenitrile Side Chain: Stereocontrolled Construction of Carbocycles with Quaternary Carbon Atoms”
Synlett 2012, 23, 251–254.

11. Yagi, H.; Chuman, Y.; Kozakai, Y.; Imagawa, T.; Takahashi, Y.; Yoshimura, F.; Tanino, K.; Sakaguchi, K.*
“A small molecule inhibitor of p53-inducible protein phosphatase PPM1D”
Bioorg. Med. Chem. Lett. 2012, 22, 729–732.

12. Yoshimura, F.; Takahashi, Y.; Tanino, K.*; Miyashita, M.*
“Synthetic Studies of the Zoanthamine Alkaloids: Total Synthesis of Zoanthenol based on an Isoaromatization Strategy”
Chem. Asian J. 2011, 6, 922–931.

13. Takahashi, Y.; Yoshimura, F.; Tanino, K.*; Miyashita, M.*
“Total Synthesis of Zoanthenol”
Angew. Chem. Int. Ed. 2009, 48, 8905−8908.

14. Yoshimura, F.; Matsui, A.; Hirai, A.; Tanino, K.; Miyashita, M.*
“Stereoselective SN2’-alkylation reaction sequence of the γ,δ-epoxy α,β-unsaturated ester system via γ,δ-chlorohydrin intermediates by the use of a R3Al-CuCN reagent”
Tetrahedron Lett. 2009, 50, 5126−5129.

15. Yoshimura, F.; Sasaki, M.; Hattori, I.; Komatsu, K.; Sakai, M.; Tanino, K.; Miyashita, M.*
“Synthetic Studies of the Zoanthamine Alkaloids: The Total Syntheses of Norzoanthamine and Zoanthamine”
Chem. Eur. J. 2009, 15, 6626–6644.

16. Yoshimura, F.; Takahashi, M.; Tanino, K.; Miyashita, M.*
“An Efficient Synthetic Method for 3-Bromofuran Derivatives via Stereoselective Cyclization of γ,δ-Epoxy-(E)-α-bromoacrylates”
Heterocycles 2009, 77, 201–206.

17. Yu, X.-Q.; Yoshimura, F.; Tanino, K.; Miyashita, M.*
“Stereospecific interconversion of cis- and trans-γ,δ-epoxy α,β-unsaturated ester systems”
Tetrahedron Lett. 2008, 49, 7442–7445.

18. Yoshimura, F.; Takahashi, M.; Tanino, K.; Miyashita, M.*
“Stereospecific epoxide-opening reactions with 1,1-dibromo-3,4-epoxy-1-alkenes with carbon nucleophiles”
Tetrahedron Lett. 2008, 49, 6991−6994.

19. Yu, X.-Q.; Yoshimura, F.; Ito, F.; Sasaki, M.; Hirai, A.; Tanino, K.; Miyashita, M.*
“Palladium-catalyzed Stereospecific Substitution of α,β-Unsaturated γ,δ-Epoxy Esters by Alcohols with Double Inversion of Configuration: Synthesis of 4-Alkoxy-5-hydroxy-2-pentenoates”
Angew. Chem. Int. Ed. 2008, 47, 750¬–754.

20. Yoshimura, F.; Lear, M. J.*; Ohashi, I.; Koyama, Y.; Hirama. M.*
“Synthesis of the entire carbon framework of the kedarcidin chromophore aglycon”
Chem. Commun. 2007, 3057−3059.

21. Hirama, M.*; Akiyama, K.*; Das, P.; Mita, T.; Lear, M. J.; Iida, K.; Sato, I.; Yoshimura, F.; Usuki, T.; Tero-Kubota, S.
“Direct Observation of ESR Spectra of Bicyclic Nine-membered Enediynes at Ambient Temperature”
Heterocycles 2006, 69, 83−89.

22. Koyama, Y.; Lear, M. J.*; Yoshimura, F.; Ohashi, I.; Mashimo, T.; Hirama, M.*
“Efficient Construction of the Kedarcidin Chromophore Ansamacrolide”
Org. Lett. 2005, 7, 267−270.

23. Rivkin, A.; Yoshimura, F.; Gabarda, A. E.; Cho. Y. S.; Chou, T.-C.; Dong, H.; Danishefsky, S. J.*
“Discovery of (E)-9,10-Dehydroepothilones through Chemical Synthesis: On the Emergence of 26-Trifluoro-(E)-9,10-dehydro-12,13-desoxyepothilone B as a Promising Anticancer Drug Candidate”
J. Am. Chem. Soc. 2004, 126, 10913−10922.

24. Usuki, T.; Mita, T.; Lear, M. J.*; Das, P.; Yoshimura, F.; Inoue, M.; Hirama, M.*; Akiyama, K.*; Tero-Kubota, S.
“Spin-Trapping of 13C-Labeled p-Benzynes Generated by Masamune-Bergman Cyclization of Bicyclic Nine-Membered Enediynes”
Angew. Chem. Int. Ed. 2004, 43, 5249−5253.

25. Ohashi, I.; Lear, M. J.*; Yoshimura, F.; Hirama, M.*
“Use of Polystyrene-Supported DBU in the Synthesis and α-Selective Glycosylation Study of the Unstable Schmidt Donor of L-Kedarosamine”
Org. Lett. 2004, 6, 719−722.

26. Chou, T.-C.; Dong, H.; Rivkin, A.; Yoshimura, F.; Gabarda, A. E.; Cho, Y. S.; Tong, W. P.; Danishefsky, S. J.*
“Design and Total Synthesis of a Superior Family of Epothilone Analogues, which Eliminate Xenograft Tumors to a Nonrelapsable State”
Angew. Chem. Int. Ed. 2003, 42, 4762−4767.

27. Yoshimura, F.; Rivkin, A.; Gabarda, A. E.; Chou, T.-C.; Dong, H.; Sukenick, G.; Morel, F. F.; Taylor, R. E.; Danishefsky, S. J.*
“Synthesis and Conformational Analysis of (E)-9,10-Dehydroepothilone B: A Suggestive Link between the Chemistry and Biology of Epothilones”
Angew. Chem. Int. Ed. 2003, 42, 2518−2521.

28. Rivkin, A.; Yoshimura, F.; Gabarda, A. E.; Chou, T.-C.; Dong, H.; Tong, W. P.; Danishefsky, S. J.*
“Complex Target-Oriented Total Synthesis in the Drug Discovery Process: The Discovery of a Highly Promising Family of Second Generation Epothilones”
J. Am. Chem. Soc. 2003, 125, 2899−2901.

29. Lear, M. J.; Yoshimura, F.; Hirama, M.*
“A Direct and Efficient α-Selective Glycosylation Protocol for the Kedarcidin Sugar, L-Mycarose: AgPF6 as a Remarkable Activator of 2-Deoxythioglycosides”
Angew. Chem. Int. Ed. 2001, 40, 946−949.

30. Yoshimura, F.; Kawata, S.; Hirama, M.*
“Synthetic study of kedarcidin chromophore: atropselective construction of the ansamacrolide”
Tetrahedron Lett. 1999, 40, 8281−8285.

31. Kawata, S.; Yoshimura, F.; Irie, J.; Ehara, H.; Hirama, M.*
“Synthetic Study of Kedarcidin Chromophore: Advanced Models and Their Chemical Behavior”
Synlett 1997, 250−252.



REVIEWS (REFEREED)
1. Yoshimura, F.*; Tanino, K.; Miyashita, M.
“Recent developments in the synthesis of zoanthamine alkaloids”
Tetrahedron Lett. 2014, 55, 2895–2903.

2. Yoshimura, F.; Tanino, K.; Miyashita, M.*
“Chemical Synthesis of Zoanthamine Alkaloids”
J. Synth. Org. Chem., Jpn. 2013, 71, 124−135.

3. Yoshimura, F.; Tanino, K.; Miyashita, M.*
“Total Synthesis of Zoanthamine Alkaloids”
Acc. Chem. Res. 2012, 45, 746–755.

4. Rivkin, A.; Cho, Y. S.; Gabarda, A. E.; Yoshimura, F.; Danishefsky, S. J.*
“Application of Ring-Closing Metathesis Reactions in the Synthesis of Epothilones”
J. Nat. Prod. 2004, 67, 139−143.



PATENTS
1. Sakaguchi, K.; Tanino, K.; Chuman, Y.; Yoshimura, F.; Yagi, H.
“Protein Phosphatase Inhibitor”
PCT Int. Appl., (2010), WO 2010041401.

2. Danishefsky, S. J.; Rivkin, A.; Yoshimura, F.; Chou, T.-C.; Gabarda, A. E.; Dong, H.; Wu, K.; Moore, M. A.; Dorn, D.
“Synthesis of Epothilones, Intermediates thereto, Analogues and Uses thereof”
PCT Int. Appl., (2005), WO 2005084222.

3. Danishefsky, S. J.; Rivkin, A.; Yoshimura, F.; Gabarda, A. E.; Cho, Y. S.; Chou, T.-C.; Dong, H.
“Synthesis of Epothilones, Intermediates thereto, Analogues and Uses thereof”
PCT Int. Appl., (2004), WO 2004018478.