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)

  • 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)

  • 2005.04
    -
    Present

    慶應義塾大学 助教(医学部)

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

  • Organic chemistry (Sythetic Organic Chemistry)

  • Basic chemistry (Crystallography)

  • Science education (The first-year experience in university)

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

  • 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.

  • Asymmetric Total Synthesis of Fasicularin by Chiral N-Alkoxyamide Strategy

    S. Yamamoto, Y. Komiya, A. Kobayashi, R. Minamikawa, T. Oishi, T. Sato, N. Chida

    Organic Letters (American Chemical Society)  21 ( 6 ) 1868 - 1871 2019.02

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

     View Summary

    © 2019 American Chemical Society. The asymmetric total synthesis of fasicularin is reported. The key to success is the use of a chiral N-alkoxyamide to control both reactivity and stereoselectivity. This functional group enables the aza-spirocyclization and the reductive Strecker reaction, which cannot be realized with an ordinary amide. In addition, use of the chiral alkoxy group establishes two consecutive stereocenters in the aza-spirocyclization through remote stereocontrol.

  • Total synthesis of (–)-zephyranthine

    Ishii K., Seki-Yoritate Y., Ishibashi M., Liaw M., T. Oishi, T. Sato, N. Chida

    Heterocycles (Heterocycles)  99 ( 1 ) 111 - 117 2018.10

    Research paper (scientific journal), Joint Work, Accepted,  ISSN  03855414

     View Summary

    © 2019 The Japan Institute of Heterocyclic Chemistry – Stereoselective total synthesis of (–)-zephyranthine 1 based on the chiral pool approach starting from D-arabinose is described. The three consecutive chiral centers in (–)-zephyranthine were effectively constructed by the sequential [3,3] sigmatropic rearrangements (Claisen, Overman, and Claisen rearrangements) with chirality transfer of the hydroxy groups in D-arabinose.

  • Crystal structure of (–)-(R,E)-3-(1,3-benzodioxol-5-yl)-5-[(4S,5R)-5-hy­droxy­methyl-2,2-dimethyl-1,3-dioxolan-4-yl]-N,N-di­methyl­pent-4-enamide

    T. Oishi, K. Ishii, M. Ishibashi, T. Sato, N. Chida

    Acta Crystallographica (International Union of Cristallographica)  E74 ( 7 ) 825 - 828 2018.05

    Research paper (scientific journal), Joint Work, Accepted,  ISSN  2056-9890

     View Summary

    © 2018 International Union of Crystallography. All rights reserved. In the title compound, C 20 H 27 NO 6 , the amide moiety is essentially planar, with a maximum deviation of 0.073(3)Å, and one of the N-methyl groups shows rotational disorder. The five-membered 1,3-dioxolane ring adopts an envelope form, with the C atom bonded to the olefin side chain as the flap, which deviates from the mean plane through the other four atoms by 0.564(7)Å. The 1,3-dioxole ring fused to the benzene ring adopts a flattened envelope form, with the C atom between the two O atoms as the flap, which deviates from the mean plane through the other four atoms by 0.215(7)Å. The C-C=C-C olefin moiety is essentially planar and makes a dihedral angle of 87.1(3)° with the benzene ring. An intramolecular O-H O hydrogen bond supports the molecular conformation, enclosing an S(11) graph-set motif. In the crystal, intermolecular C-H O hydrogen bonding links the molecules into a tape running along the b axis. Furthermore, other weak C-H;O hydrogen bonds and a C-Hπ interaction connect the tapes into a sheet structure parallel to (100).

  • Crystal structure of (–)-(5R,7R,8S,9R,10S)-8-methyl-7-[(5R)-3-methyl-2-oxooxolan-3-en-5-yl]-1-aza-6-oxatricyclo[8.3.0.05,9]tridecan-13-one monohydrate

    T. Oishi, M. Yoritate, T. Sato and N. Chida

    Acta Crystallographica (International Union of Crystallography)  E74 ( 4 ) 555 - 558 2018.03

    Research paper (scientific journal), Joint Work, Accepted,  ISSN  2056-9890

     View Summary

    © 2018 Oishi et al. The title compound, C17 H23 NO4 ·H2 O, is an epimer of the natural tetracyclic alkaloid isosaxorumamide which consists of a fused 5-7-5 tricyclic core and a dihydrofuranone substituent. The terminal dihydrofuran ring is essentially planar with a maximum deviation of 0.0273(14)Å from the mean plane and oxolane, azepane and pyrrolidine rings in the tricyclic ring system adopt twist, twist-chair and envelope forms, respectively. In the crystal, the amide and water molecules are linked by O - H...O hydrogen bonds, forming a tape structure running along the b-axis direction. The tapes are further connected by C - H...O interactions into a three-dimensional architecture.

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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

    Introduction and explanation (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, 久保田真理, Research grant, Co-investigator

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: Awards of National Conference, Council and Symposium

 

Courses Taught 【 Display / hide

  • LABORATORY OF CHEMISTRY

    2021

  • CHEMISTRY 2

    2021

  • LABORATORY OF CHEMISTRY

    2020

  • CHEMISTRY 2

    2020

  • LABORATORY OF CHEMISTRY

    2019

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Courses Previously Taught 【 Display / hide

  • 化学実験

    Keio University, 2018, Full academic year, General education subject, Laboratory work/practical work/exercise, Within own faculty, 2h, 118people

    実験,化学

  • 化学2

    Keio University, 2018, Autumn Semester, General education subject, Lecture, Outside own faculty (within Keio), 2h, 118people

    命名法,機器分析

  • 化学実験

    Keio University, 2017, Full academic year, General education subject, Laboratory work/practical work/exercise, Within own faculty, 2h, 115people

    化学,実験

  • 化学2

    Keio University, 2017, Autumn Semester, General education subject, Lecture, Lecturer outside of Keio, 2h

    有機化学

  • 化学2

    Keio University, 2016, Autumn Semester, General education subject, 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