OISHI Takeshi

写真a

Affiliation

School of Medicine (Hiyoshi)

Position

Research Associate/Assistant Professor/Instructor

Career 【 Display / hide

  • 2002.04
    -
    2003.03

    慶應義塾大学 助手(文学部/嘱託)

  • 2002.04
    -
    2003.03

    慶應義塾大学 助手(文学部/嘱託)

  • 2003.04
    -
    2004.12

    産業技術総合研究所 博士研究員(NEDOフェロー兼務)

  • 2003.04
    -
    2004.12

    産業技術総合研究所 博士研究員(NEDOフェロー兼務)

  • 2005.01
    -
    2005.03

    慶應義塾大学 准訪問研究員(理工学部)

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Academic Background 【 Display / hide

  • 1997.03

    Keio University, Faculty of Science and Technology, Department of Applied Chemistry

    University, Graduated

  • 1997.04
    -
    1999.03

    Keio University, Graduate School, Division of Science and Technology, Department of Applied Chemistry

    Graduate School, Completed, Master's course

  • 1999.04
    -
    2002.03

    Keio University, Graduate School, Division of Science and Technology, Department of Applied Chemistry

    Graduate School, Withdrawal after completion of doctoral course requirements, Doctoral course

Academic Degrees 【 Display / hide

  • 博士(工学), Keio University, Coursework, 2002.10

 

Research Areas 【 Display / hide

  • Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry (Sythetic Organic Chemistry)

  • Life Science / Bioorganic chemistry (Sythetic Organic Chemistry)

  • Nanotechnology/Materials / Fundamental physical chemistry (Crystallography)

  • Humanities & Social Sciences / Science education (The first-year experience in university)

  • Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry

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Research Keywords 【 Display / hide

  • 大学初年次教育

  • synthesis of natural products

  • 結晶学

Research Themes 【 Display / hide

  • elucidation of relevance between the mechanism for crystallization of bioactive product and their structure-activity-relationship, 

    2012
    -
    Present

  • 論理的思考力を養う学生実験の開発, 

    2011
    -
    Present

 

Papers 【 Display / hide

  • Lactam Strategy Using Amide-Selective Nucleophilic Addition for Quick Access to Complex Amines: Unified Total Synthesis of Stemoamide-Type Alkaloids

    Sugiyama Yasukazu, Soda Yasuki, Yoritate Makoto, Tajima Hayato, Takahashi Yoshito, Shibuya Kana, Ogihara Chisato, Yokoyama Takashi, Oishi Takeshi, Sato Takaaki, Chida Noritaka

    Bulletin of the Chemical Society of Japan (The Chemical Society of Japan)  95 ( 2 ) 278 - 287 2022

    ISSN  00092673

     View Summary

    <p>Our research group has been exploring a lactam strategy for the concise total synthesis of complex alkaloids. In this article, we report full details of the unified total synthesis of stemoamide-type alkaloids by chemoselective assembly of five-membered rings based on the lactam strategy. First, the concise and gram-scale synthesis of tricyclic stemoamide was achieved by vinylogous Michael addition-reduction sequence of an unsaturated γ-lactam with an unsaturated γ-lactone, followed by <i>N</i>-alkylation to form the seven-membered ring. From stemoamide as a common intermediate, chemoselective nucleophilic addition of unsaturated lactone derivatives provides tetracyclic natural products. While stemonine is obtained by an Ir-catalyzed lactam-selective reductive Mannich reaction, saxorumamide and isosaxorumamide are produced through the lactone-selective nucleophilic addition of the lithiated 2-silyl furan. The developed conditions for the lactam-selective nucleophilic reactions are highly general, and were found to be applicable to the total synthesis of pentacyclic stemocochinin and isostemocochinin. The strategy enables the concise and unified total synthesis of tricyclic, tetracyclic and pentacyclic stemoamide-type alkaloids within 12 steps from a commercially available compound.</p>

  • Total Synthesis and Anti-inflammatory Activity of Stemoamide-Type Alkaloids Including Totally Substituted Butenolides and Pyrroles

    Soda Y., Sugiyama Y., Sato S., Shibuya K., Saegusa J., Matagawa T., Kawano S., Yoritate M., Fukaya K., Urabe D., Oishi T., Mori K., Simizu S., Chida N., Sato T.

    Synthesis (Germany) (Synthesis (Germany))   2022

    ISSN  00397881

     View Summary

    The totally substituted butenolide including two tetrasubstituted olefins is a distinct structural motif seen in Stemona alkaloids, but efficient methods for its synthesis are not well developed. As an ongoing program aimed at the collective total synthesis of the stemoamide group, we report a stereodivergent method to give either (E)-or (Z)-totally substituted butenolide from the same intermediate. While the AgOTf-mediated elimination via the E1-type mechanism results in the formation of the kinetic (Z)-tetrasubstituted olefin, the subsequent TfOH-mediated isomerization gives the thermodynamic (E)-tetrasubstituted olefin. The pyrrole ring is another important structure found in Stemona alkaloids. The direct oxidation of pyrrolidine rings with MnO2 and careful purification give the pyrrole groups without isomerization of the stereocenter in the lactone group. These two methods enable us to synthesize a series of stemoamide-type alkaloids including tricyclic, tetracyclic and pentacyclic frameworks. The anti-inflammatory activities by inhibition of iNOS expression in macrophage cell line RAW264.7 indicate that the most potent anti-inflammatory compounds without cytotoxicity are protostemonines, which consist of pentacyclic frameworks including the totally substituted butenolide.

  • Crystal structure of (+)-(1S,5S,6S,7S,10S,11S,16S)-16-hy droxy-7-(meth oxy meth oxy)-11,15,18,18-tetra methyl-3,13-dioxo-2,4-dioxa tetra cyclo[12.3.1.0<sup>1,5</sup>.0<sup>6,11</sup>]octa dec-14-en-10-yl benzoate

    Oishi T., Fukaya K., Sato T., Chida N.

    Acta Crystallographica Section E: Crystallographic Communications (Acta Crystallographica Section E: Crystallographic Communications)  77   1234 - 1238 2021.12

    ISSN  2056-9890

     View Summary

    In the fused tetra cyclic system of the title compound, C29H36O9, the five-membered dioxolane ring adopts a twist conformation; the two adjacent C atoms deviate alternately from the mean plane of the other three atoms by -0.252 (6) and 0.340 (6) Å. The cyclo hexane, cyclo hexene and central cyclo octane rings show chair, half-chair and boat-chair forms, respectively. There are three intra molecular C - H⋯O inter actions supporting the mol ecular conformation, with one S(6) and two S(7) graph-set motifs. In the crystal, inter molecular O - H⋯O hydrogen bonds connect the mol ecules into a helical chain running along the c-axis direction, generating a C(7) graph-set motif. The chains are further linked by inter molecular C - H⋯O inter actions to construct a three-dimensional network. There is no valid C - H⋯π inter action.

  • Total Synthesis of Paclitaxel

    Iiyama S., Fukaya K., Yamaguchi Y., Watanabe A., Yamamoto H., Mochizuki S., Saio R., Noguchi T., Oishi T., Sato T., Chida N.

    Organic Letters (Organic Letters)  24 ( 1 ) 202 - 206 2021

    ISSN  15237060

     View Summary

    The total synthesis of paclitaxel (Taxol) is described. Double Rubottom oxidation of the bis(silyl enol ether) derived from a tricarbocyclic diketone effectively installed a bridgehead olefin and C-5/C-13 hydroxy groups in a one-step operation. The novel Ag-promoted oxetane formation smoothly constructed the tetracyclic framework of paclitaxel.

  • Unified Total Synthesis of Pentacyclic Stemoamide-type Alkaloids

    Soda Y., Sugiyama Y., Yoritate M., Tajima H., Shibuya K., Ogihara C., Oishi T., Sato T., Chida N.

    Organic Letters (Organic Letters)  22 ( 19 ) 7502 - 7507 2020.10

    Research paper (scientific journal), Joint Work, Accepted,  ISSN  15237060

     View Summary

    The collective synthesis of pentacyclic stemoamide-type alkaloids is recognized as a daunting task despite high demand for a comprehensive biological profiling of these natural products. In this Letter, we report a unified synthesis of seven pentacyclic alkaloids and two unnatural derivatives. The keys to success are (1) the chemoselective assembly of four five-membered building blocks, (2) the direct oxidation of pyrrolidine natural products to pyrrole derivatives, and (3) the stereodivergent construction of totally E- or Z-substituted butenolides.

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Papers, etc., Registered in KOARA 【 Display / hide

Reviews, Commentaries, etc. 【 Display / hide

  • Total syntheses of natural products containing alpha-substituted alpha-amino acid structures from aldohexoses using Overman rearrangement as the key reaction

    H. Sato, T. Oishi, N. Chida

    Journal of Synthetic Organic Chemistry Japan (The Society of Synthetic Organic Chemistry, Japan)  62 ( 7 ) 693 - 704 2004.02

    Article, review, commentary, editorial, etc. (scientific journal), Joint Work,  ISSN  0037-9980

Presentations 【 Display / hide

  • 動画を活用した実験指導

    久保田 真理,大石 毅

    日本化学会 第92春季年会 (慶應義塾大学 日吉/矢上キャンパス) , 

    2012.03

    Oral presentation (general)

  • 動画を用いた初年次学生実験ガイダンス −リアルタイム動画とストリーミング動画の活用−

    久保田真理,大石 毅

    初年次教育学会 第4回大会 (久留米大学 御井キャンパス) , 

    2011.08

    Oral presentation (general)

  • Environmentally-benign photochemical bleaching of cotton fabric

    A. Ouchi, T. Obata, H. sakai, T. Oishi, T. Hayashi, W. Ando, J. Ito

    Korea-Japan Symposium on Frontier Photoscience "Photochemistry and Nanotechnology" (Daejeon (Korea)) , 

    2004.11

    Oral presentation (general)

  • 1,6-(N-フェニル)アザ-[60]フラーロイドの光化学的転位反応における置換フェニル基の立体効果

    A. Ouchi, B. Z. S. Awen, T. Oishi, H. X. Luo, Y. Araki, O. Ito

    2004年度光化学討論会 (つくば) , 

    2004.11

    Oral presentation (general), 光化学協会

  • 水素化ホウ素ナトリウムを用いたフラボンの光還元反応

    A. Ouchi, A. Saruwatari, T. Suzuki, T. Oishi, H. Sakai

    2004年度光化学討論会 (つくば) , 

    2004.11

    Oral presentation (general), 光化学協会

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Research Projects of Competitive Funds, etc. 【 Display / hide

  • 論理的思考力を養うための PBL 型実験の開発

    2018.08
    -
    2020.03

    大学IR総研, Research grant, Coinvestigator(s)

Awards 【 Display / hide

  • BCSJ賞(論文賞)

    T. Oishi, K. Ando, K. Inomiya, M. Iida, H. Sato, N. Chida, 2002.03, Chemical Society of Japan, Total synthesis of (+)-myriocin and (-)-sphingofungin E from aldohexoses using Overman rearrangement as the key reaction

    Type of Award: Award from Japanese society, conference, symposium, etc.

  • BCSJ賞(論文賞)

    T. Oishi, K. Ando, K. Inomiya, M. Iida, H. Sato, N. Chida, 2002.03, Chemical Society of Japan, Total synthesis of (+)-myriocin and (-)-sphingofungin E from aldohexoses using Overman rearrangement as the key reaction

    Type of Award: Award from Japanese society, conference, symposium, etc.

 

Courses Taught 【 Display / hide

  • LABORATORY OF CHEMISTRY

    2023

  • CHEMISTRY 2

    2023

  • LABORATORY OF CHEMISTRY

    2022

  • CHEMISTRY 2

    2022

  • LABORATORY OF CHEMISTRY

    2021

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Courses Previously Taught 【 Display / hide

  • 化学実験

    Keio University

    2018.04
    -
    2019.03

    Full academic year, Laboratory work/practical work/exercise, Within own faculty, 2h, 118people

    実験,化学

  • 化学2

    Keio University

    2018.04
    -
    2019.03

    Autumn Semester, Lecture, Outside own faculty (within Keio), 2h, 118people

    命名法,機器分析

  • 化学実験

    Keio University

    2017.04
    -
    2018.03

    Full academic year, Laboratory work/practical work/exercise, Within own faculty, 2h, 115people

    化学,実験

  • 化学2

    Keio University

    2017.04
    -
    2018.03

    Autumn Semester, Lecture, Lecturer outside of Keio, 2h

    有機化学

  • 化学2

    Keio University

    2016.04
    -
    2017.03

    Autumn Semester, Lecture, Lecturer outside of Keio, 2h

    有機化学

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Educational Activities and Special Notes 【 Display / hide

  • 日本・スウェーデン高校生合同 化学実験体験プログラム(講義・実習)

    2019.05

    , Special Affairs

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    平成31年度JSTグローバルサイエンスキャンパス事業

  • 平成30年度 JST全国受講生研究発表会 審査員

    2018.10

    , Special Affairs

  • 日本・スウェーデン高校生合同 化学実験体験プログラム(講義・実習)

    2018.03

    , Special Affairs

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    平成29年度JSTグローバルサイエンスキャンパス事業

  • 日本・スウェーデン高校生合同 化学実験体験プログラム(講義・実習)

    2017.05

    , Special Affairs

     View Details

    平成29年度JSTグローバルサイエンスキャンパス事業

  • 平成28年度 JST全国受講生研究発表会 審査員

    2016.09

    , Special Affairs

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Memberships in Academic Societies 【 Display / hide

  • 初年次教育学会, 

    2019
    -
    Present
  • 有機合成化学協会, 

    2000
    -
    Present
  • 日本化学会, 

    2000
    -
    Present

Committee Experiences 【 Display / hide

  • 2000

    Member, 日本化学会

  • 2000

    会員, 有機合成化学協会

  • 2000

    会員, 日本化学会

  • 2000

    Member, 有機合成化学協会