Fumihiko Yoshimura, Ph.D.
Curriculum Vitae
Associate Professor
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://us-yakuzo.jp/
ORCID: 0000-0002-1187-6062
ReseacherID: A-4116-2012

Born: 9 March 1974RESEARCH FOCUS• Total synthesis of biologically active natural products with quaternary asymmetric carbon centers• Development of novel synthetic methods• Molecular design and synthesis of probe molecules for elucidation of biological functions
PROFESSIONAL EXPERIENCE
University of Shizuoka, Shizuoka, Japan (May 2017–Present)• Associate Professor (Laboratory of Professors Toshiyuki Kan and Ryo Takita)
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)• Postdoctoral Research 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

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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 OrganicChemistry in Asia (2006)• Uehara Memorial Foundation Postdoctoral Fellowship (2002−2003)• JSPS Research Fellowship for Young Scientist (DC1) (1998−2001)
RESEARCH PUBLICATIONS (REFEREED)
1.

Nishizawa, S.; Ouchi, H.*; Suzuki, H.; Ohnishi, T.; Sasaki, S.; Oyagi, Y.; Kanakogi, M.; Matsumura, Y.;
Nakagawa, S.; Asakawa, T.; Egi, M.; Inai, M.; Yoshimura, F.; Takita, R.; Kan, T.*“Total Synthesis of (–)-Domoic Acid, A Potent Ionotropic Glutamate Receptor Agonist and the Key
Compound in Oceanic Harmful Algal Blooms”
Org. Biomol. Chem. 2023, 21, 1653–1656.

2.

Kamada, R.; Uno, S.; Kimura, N.; Yoshimura, F.; Tanino, K.; Sakaguchi, K.*“Lipid Droplet Formation is Regulated by Ser/Thr Phosphatase PPM1D via Dephosphorylation ofPerilipin 1”
Int. J. Mol. Sci. 2022, 23, 12046.

3.

Inai, M.*; Ueno, Y.; Sagara, H.; Ouchi, H.; Yoshimura, F.; Kan, T.*“Total Synthesis of Isosilybin B”
Eur. J. Org. Chem. 2022, e202200653.

4.

Murakami, H.; Asakawa, T.; Muramatsu, Y.; Ishikawa, R.; Hiza, A.; Tsukaguchi, Y.; Tokumaru, Y.; Egi,M.; Inai, M.; Ouchi, H.; Yoshimura, F.; Taniguchi, T.; Ishikawa, Y.; Kondo, M.; Kan, T.*“Total Synthesis of Sophoraflavanone H and Confirmation of Its Absolute Configuration”
Org. Lett. 2020, 22, 3820–3824.

5.

Miura, Y.; Ouchi, H.; Inai, M.; Osawa, T.; Yoshimura, F.; Kanazawa, J.; Uchiyama, M.; Kondo, M.; Kan,T.*“Synthetic Studies on Pactamycin: A Synthesis of Johnson’s Intermediate”
Org. Lett. 2020, 22, 3515–3518.

6.

Ohmi, K.; Miura, Y.; Nakao, Y.; Goto, A.; Yoshimura, S.; Ouchi, H.; Inai, M.*; Asakawa, T.; Yoshimura,F.; Kondo, M.; Kan, T.*“Pactamycin and its Derivatives: Improved Synthesis Route”
Eur. J. Org. Chem. 2020, 488–491.

7.

Kobayashi, M.; Ueno, H.; Yoshida, N.; Ouchi, H.; Asakawa, T.; Yoshimura, F.; Inai, M.*; Kan, T.*“Diastereodivergent and Regiodivergent Total Synthesis of Princepin and Isoprincepin in Both (7”R,8”R)and (7”S,8”S) Isomers”
J. Org. Chem. 2019, 84, 14227–14240.

8.

Kamada, R.; Kimura, N.; Yoshimura, F.; Tanino, K.; Sakaguchi, K.*“Inhibition of lipid droplet formation by Ser/Thr protein phosphatase PPM1D inhibitor, SL-176”
PLoS ONE 2019, 14, e0212682.

9.

Yoshimura, F.*; Okada, T.; Tanino, K.*“Asymmetric Total Synthesis of Laurallene”
Org. Lett. 2019, 21, 559–562.

210. Yoshimura, F.*; Abe, T.; Ishioka, Y.; Tanino, K.*“Synthetic study of andrastins: Stereoselective construction of the BCD-ring system”
J. Antibiot. 2019, 72, 384–388.
11. Yoshimura, F.*; Itoh, R.; Torizuka, M.; Mori, G.; Tanino, K.*“Asymmetric Total Synthesis of Brasilicardins”
Angew. Chem. Int. Ed. 2018, 57, 17161–17167.
12. Yoshimura, F.*; Saito, H.; Abe, T.; Tanino, K.*“Nucleophilic Addition of Alkanenitriles to Aldehydes via N-Silyl Ketene Imines Generated In Situ”
Synlett 2017, 28, 1816–1820.
13. 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, 162, 303–308.
14. 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.
15. 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.
16. 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 humancolorectal carcinoma cell line”
Bioorg. Med. Chem. Lett. 2014, 24, 5593–5596.
17. Yoshimura, F.*; Abe, T.; Tanino, K.*“Nucleophilic Addition Reactions of Nitriles to Nitrones under Mild Silylation Conditions”
Synlett 2014, 25, 1863–1868.
18. Tanino, K.*; Yamada. T.; Yoshimura, F.; Suzuki, T.*“Cyanoazulene-based Multistage Redox Systems Prepared from Vinylcyclopropanecarbonitrile andCyclopentenone via Divinylcyclopropane-rearrangement Approach”
Chem. Lett. 2014, 43, 607–609.
19. Yamada. T.; Yoshimura, F.; Tanino, K.*“Synthesis of 2-cyano-1,4-cycloheptadiene derivatives via divinylcyclopropane rearrangement andalkylation of novel cycloheptadienyl anion species”
Tetrahedron Lett. 2013, 54, 522–525.
20. Yoshimura, F.*; Kowata, A.; Tanino, K.*“Stereocontrolled synthesis of carbocyclic compounds with a quaternary carbon atom based on SN2’
alkylation of g,d-epoxy-a,b-unsaturated ketones”
Org. Biomol. Chem. 2012, 10, 5431–5442.
21. Yoshimura, F.*; Torizuka, M.; Mori, G.; Tanino, K.*“Intramolecular Conjugate Addition of a,b-Unsaturated Lactones Having an Alkanenitrile Side Chain:
Stereocontrolled Construction of Carbocycles with Quaternary Carbon Atoms”
Synlett 2012, 23, 251–254.

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22. 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.
23. 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.
24. Takahashi, Y.; Yoshimura, F.; Tanino, K.*; Miyashita, M.*“Total Synthesis of Zoanthenol”
Angew. Chem. Int. Ed. 2009, 48, 8905−8908.
25. Yoshimura, F.; Matsui, A.; Hirai, A.; Tanino, K.; Miyashita, M.*“Stereoselective SN2’-alkylation reaction sequence of the g,d-epoxy a,b-unsaturated ester system via g,dchlorohydrin intermediates by the use of a R3Al-CuCN reagent”
Tetrahedron Lett. 2009, 50, 5126−5129.
26. 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 andZoanthamine”
Chem. Eur. J. 2009, 15, 6626–6644.
27. Yoshimura, F.; Takahashi, M.; Tanino, K.; Miyashita, M.*“An Efficient Synthetic Method for 3-Bromofuran Derivatives via Stereoselective Cyclization of g,dEpoxy-(E)-a-bromoacrylates”
Heterocycles 2009, 77, 201–206.
28. Yu, X.-Q.; Yoshimura, F.; Tanino, K.; Miyashita, M.*“Stereospecific interconversion of cis- and trans-g,d-epoxy a,b-unsaturated ester systems”
Tetrahedron Lett. 2008, 49, 7442–7445.
29. 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.
30. Yu, X.-Q.; Yoshimura, F.; Ito, F.; Sasaki, M.; Hirai, A.; Tanino, K.; Miyashita, M.*“Palladium-catalyzed Stereospecific Substitution of a,b-Unsaturated g,d-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.
31. 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.
32. 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.
33. 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.

434. 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 26Trifluoro-(E)-9,10-dehydro-12,13-desoxyepothilone B as a Promising Anticancer Drug Candidate”
J. Am. Chem. Soc. 2004, 126, 10913−10922.
35. Usuki, T.; Mita, T.; Lear, M. J.*; Das, P.; Yoshimura, F.; Inoue, M.; Hirama, M.*; Akiyama, K.*; TeroKubota, 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.
36. Ohashi, I.; Lear, M. J.*; Yoshimura, F.; Hirama, M.*“Use of Polystyrene-Supported DBU in the Synthesis and a-Selective Glycosylation Study of theUnstable Schmidt Donor of L-Kedarosamine”
Org. Lett. 2004, 6, 719−722.
37. 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.
38. 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.
39. 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.
40. Lear, M. J.; Yoshimura, F.; Hirama, M.*“A Direct and Efficient a-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.
41. Yoshimura, F.; Kawata, S.; Hirama, M.*“Synthetic study of kedarcidin chromophore: atropselective construction of the ansamacrolide”
Tetrahedron Lett. 1999, 40, 8281−8285.
42. 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.*; Itoh, R.; Torizuka, M.; Mori, G.; Tanino, K.*“Chemical Synthesis of Brasilicardins”
J. Synth. Org. Chem., Jpn. 2020, 78, 1085−1093.

2.

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

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3.

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

4.

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

5.

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.

BOOKS
1.

Okada, T.; Yoshimura, F.
“Bis[5,5-dimethyl-1-(4-methylpiperazin- 1-yl)-1,2,4-hexanetrionato-𝜿2O,𝜿4O] cobalt(II)”Encyclopedia of Reagents for Organic Synthesis (e-EROS), 2022,
doi: 10.1002/047084289X.rn02474

BOOKS (JAPANESE)
1.

吉村文彦, 高井和彦
“高井反応”
天然物合成で活躍した反応, 有機合成化学協会 編, 化学同人,2011, pp 8–9.

2.

吉村文彦, 谷野圭持
“伊藤-三枝酸化”，“オレフィン化”，“三成分連結反応”，“光学活性アリルシランの合成と反応”，“SN2’ および SN2 反応”，
“Trost 酸化と TPAP 酸化”“エポキシドのアリルアルコールへの変換とオゾン酸化”，“一重項酸素酸化”
天然物合成で活躍した反応, 有機合成化学協会 編, 化学同人,2011, pp 26–27; pp 28–29; pp44–45; pp 80–81; pp 94–95; pp 118–119; pp 128–129; pp 132–133.

3.

宮下正昭, 谷野圭持, 吉村文彦
“ゾアンタミン系アルカロイドの全合成研究”
天然物全合成の最新動向, 監修 北泰行, シーエムシー出版,2009, pp 191–212.

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