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Stereocontrolled synthesis of poly-substituted medium-sized cyclic compounds by electrocyclic ring opening reaction and the synthesis of biologically active molecules

Research Project

Project/Area Number 16H05073
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionKyoto University

Principal Investigator

Takasu Kiyosei  京都大学, 薬学研究科, 教授 (10302168)

Co-Investigator(Kenkyū-buntansha) 服部 明  京都大学, 薬学研究科, 准教授 (50300893)
山岡 庸介  京都大学, 薬学研究科, 助教 (60624723)
Research Collaborator Shimoda Kazuma  
Ito Tomohiro  
Ogawa Naoki  
Tsutsumi Masaki  
Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥18,200,000 (Direct Cost: ¥14,000,000、Indirect Cost: ¥4,200,000)
Fiscal Year 2018: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000)
Fiscal Year 2017: ¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2016: ¥9,490,000 (Direct Cost: ¥7,300,000、Indirect Cost: ¥2,190,000)
Keywords分子ひずみ / 中員環化合物 / 小員環化合物 / 医薬候補化合物 / 有機材料 / 反応開発 / シクロブタン / シクロブテン / キラリティ / 生理活性天然物 / 中員環 / 面性不斉 / シクロプロパン / シクロブタノン / ヘリセン / 新規反応 / 小員環 / 電子環状反応 / 不斉合成 / 生物活性分子
Outline of Final Research Achievements

For the drug discovery of small molecule drugs with new chemical space, we focused on the strained molecules such as small an medium-sized cyclic molecules. In this project, we investigated the new synthetic methods to afford such molecules and analyzed evaluated the physical, optical, chemical and biological characters of the synthetic compounds. Based on these findings, we designed useful substances and examined the search for drug and pesticide candidate compounds and organic materials. In particular, very advanced findings have been obtained on the chemistry of medium-ring trans cycloalkenes.

Academic Significance and Societal Importance of the Research Achievements

本研究を遂行することにより、これまで選択的・効率的合成法が限定的であった中員環や小員環などのひずみ化合物を実践的な条件で合成できることが明らかになった。さらに、合成した分子には医薬化学的もしくは材料化学的に潜在的有用性があることが明らかになった。これらの基盤に、抗腫瘍活性や植物成長活性を有する天然物および誘導体を開発することができ、今後の研究発展により実用化につながると期待できるようになった。また、外部環境により色調や蛍光が変化する有機材料候補の創出にも成功した。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Annual Research Report
  • 2016 Annual Research Report
  • Research Products

    (33 results)

All 2019 2018 2017 2016 Other

All Int'l Joint Research (3 results) Journal Article (12 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 12 results,  Open Access: 1 results,  Acknowledgement Compliant: 4 results) Presentation (16 results) (of which Int'l Joint Research: 7 results,  Invited: 8 results) Book (2 results)

  • [Int'l Joint Research] カンザス州立大学(米国)

    • Related Report
      2018 Annual Research Report
  • [Int'l Joint Research] マックスプランク石炭化学研究所(ドイツ)

    • Related Report
      2018 Annual Research Report
  • [Int'l Joint Research] カンザス州立大学(米国)

    • Related Report
      2017 Annual Research Report
  • [Journal Article] Optical resolution via catalytic generation of chiral auxiliary2019

    • Author(s)
      Kiyama Hiroki、Inokuma Tsubasa、Kuroda Yusuke、Yamaoka Yousuke、Takasu Kiyosei、Yamada Ken-ichi
    • Journal Title

      Tetrahedron Letters

      Volume: 60 Issue: 2 Pages: 175-177

    • DOI

      10.1016/j.tetlet.2018.12.006

    • NAID

      120006937697

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Properties of Tribenzocarbazoles via an Acid-Promoted Retro (2+2)-Cycloaddition of Azapropellanes2018

    • Author(s)
      Ogawa Naoki、Yamaoka Yousuke、Takikawa Hiroshi、Tsubaki Kazunori、Takasu Kiyosei
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 83 Issue: 15 Pages: 7994-8002

    • DOI

      10.1021/acs.joc.8b00870

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Silyl enol etherification by a Tf2NH/amine co-catalytic system for minimizing hazardous waste generation2018

    • Author(s)
      Kurahashi Kei、Yamaoka Yousuke、Takemoto Yoshiji、Takasu Kiyosei
    • Journal Title

      Reaction Chemistry & Engineering

      Volume: 3 Issue: 5 Pages: 626-630

    • DOI

      10.1039/c8re00039e

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Azaheterocycles and Related Molecules by Tf2NH-Catalyzed Cycloadditions2018

    • Author(s)
      Shindo Naoya、Takasu Kiyosei
    • Journal Title

      HETEROCYCLES

      Volume: 96 Issue: 2 Pages: 195-218

    • DOI

      10.3987/rev-17-875

    • Related Report
      2018 Annual Research Report 2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Multi-substituted Cyclobutenes: Cyclic Strategy for (2+2) Cycloaddition of Ketene Silyl Acetals with Propiolates2017

    • Author(s)
      Y. Yamaoka, M. Ueda, T. Yamashita, K. Shimoda, K. Yamada, K. Takasu
    • Journal Title

      Tetrahedron Lett

      Volume: 58 Issue: 30 Pages: 2944-2947

    • DOI

      10.1016/j.tetlet.2017.06.039

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of pai-Extended Fluoranthenes via a KHMDS-Promoted Anion and Radical Reaction Cascade2017

    • Author(s)
      N. Ogawa, Y. Yamaoka, K. Yamada, K. Takasu
    • Journal Title

      Org. Lett.

      Volume: 19 Issue: 12 Pages: 3327-3330

    • DOI

      10.1021/acs.orglett.7b01538

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and biological evaluation of steroidal derivatives bearing a small ring as vitamin D receptor agonists2017

    • Author(s)
      N. Arichi, S. Fujiwara, M. Ishizawa, M. Makishima, D. H. Hua, K. Yamada, Y. Yamaoka, K. Takasu
    • Journal Title

      Bioorg. Med. Chem. Lett.

      Volume: 27 Issue: 15 Pages: 3408-3411

    • DOI

      10.1016/j.bmcl.2017.05.089

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Site-selective Benzoin-type Cyclization of Unsymmetrical Dialdoses Catalyzed by N-Heterocyclic Carbenes for Divergent Cyclitol Synthesis.2017

    • Author(s)
      Bubwoon Kang, Yinli Wang, Satoru Kuwano, Yousuke Yamaoka, Kiyosei Takasu, Ken-ichi Yamada
    • Journal Title

      Chem. Commun.

      Volume: 印刷中 Issue: 32 Pages: 4469-4472

    • DOI

      10.1039/c7cc01191a

    • NAID

      120006650105

    • Related Report
      2017 Annual Research Report 2016 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Total Synthesis of (-)-Histrionicotoxin through a Stereoselective Radical Translocation-Cyclization Reaction2017

    • Author(s)
      M. Sato, H. Azuma, A. Daigaku, S. Sato, K. Takasu, K. Okano, H. Tokuyama
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 56 Issue: 4 Pages: 1087-1091

    • DOI

      10.1002/anie.201609941

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Use of a Catalytic Chiral Leaving Group for Asymmetric Substitutions at sp3-Hybridized Carbon Atoms: Kinetic Resolution of β-Amino Alcohols by p-Methoxybenzylation.2016

    • Author(s)
      K. Yamada
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 55 Issue: 42 Pages: 13137-13141

    • DOI

      10.1002/anie.201607208

    • NAID

      120006556299

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Desymmetrization of Acid Anhydride with Asymmetric Esterification Catalyzed by Chiral Phosphoric Acid.2016

    • Author(s)
      K. Yamada
    • Journal Title

      Tetrahedron Lett.

      Volume: 57 Issue: 36 Pages: 4098-4100

    • DOI

      10.1016/j.tetlet.2016.07.093

    • NAID

      120006650106

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] 2.Synthesis of Multisubstituted Silyloxy-based Donor-Acceptor Cyclobutanes by an Acid-Catalyzed [2+2] Cycloaddition2016

    • Author(s)
      Takasu, K.
    • Journal Title

      Israel J. Chem.

      Volume: 56 Issue: 6-7 Pages: 488-498

    • DOI

      10.1002/ijch.201500096

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 電子環状反応を利用したtrans-シクロアルケンの新規合成法とその応用2018

    • Author(s)
      伊藤 智裕, 堤 正貴, 瀧川 紘, 山田 健一, 山岡 庸介, 高須 清誠
    • Organizer
      モレキュラーキラリティ2018
    • Related Report
      2018 Annual Research Report
  • [Presentation] Synthesis and Properties of Tribenzocarbazoles via an Acid Promoted Retro (2+2)-Cycloaddition of Azapropellanes2018

    • Author(s)
      Naoki Ogawa, Yousuke Yamaoka. Hiroshi Takikawa, Kiyosei Takasu
    • Organizer
      International Symposium on Main Group Chemistry Directed towards Organic Synthesis (MACOS)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 植物の成長を制御するプロトイルダン類の合成2018

    • Author(s)
      下田和摩、山岡庸介、瀧川紘、山田健一、高須清誠
    • Organizer
      第60回天然有機化合物討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 合成しにくそうな分子構造をどう作ってどう使うか?2018

    • Author(s)
      高須清誠
    • Organizer
      金沢大学薬学シンポジウム2018
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Total Synthesis of Biologically Active Protoilludane Sesquiterpenes2018

    • Author(s)
      Kiyosei Takasu
    • Organizer
      The 13th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-13)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 植物成長活性を有するmelleolideの合成研究2017

    • Author(s)
      下田和摩、山岡庸介、山田健一、高須清誠
    • Organizer
      創薬懇話会2017
    • Related Report
      2017 Annual Research Report
  • [Presentation] An Arylative Ring Expansion Cascade of Fused Cyclobutenes2017

    • Author(s)
      Norihito Arichi, Yousuke Yamaoka, Ken-ichi Yamada, Kiyosei Takasu
    • Organizer
      26th ISHC Congress
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 分子ひずみの付加と解消を利用する有機合成2017

    • Author(s)
      高須清誠
    • Organizer
      神戸大学大学院理学研究科セミナー
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Total Syntheses of Cyclobutane-containing Natural Products2017

    • Author(s)
      Kiyosei Takasu
    • Organizer
      7th Sino-Japanese Symposium on Organic Chemistry for Young Scientists
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 細胞内微小環境の差を認識する抗マラリア剤・抗がん剤の設計にむけて2017

    • Author(s)
      高須清誠
    • Organizer
      第4回臨床薬学懇話会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Total Synthesis of Echinocidin D by Using Lewis Acid Catalyzed [2+2] Cycloaddition2017

    • Author(s)
      Kazuma Shimoda, Yousuke Yamaoka, Hiroshi Takikawa, Ken-ichi Yamada, Kiyosei Takasu
    • Organizer
      The Eleventh International Symposium on Integrated Synthesis(ISONIS-11)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of Medium-sized trans-Cycloalkenes by Domino 4p-Electrocyclization-Alkylation of Fused Cyclobutenes2016

    • Author(s)
      Tomohiro Ito, Ken-ichi Yamada, Yousuke Yamaoka, Kiyosei Takasu
    • Organizer
      The Tenth International Symposium on Integrated Synthesis(ISONIS-10)
    • Place of Presentation
      Awaji Umebutai
    • Year and Date
      2016-11-18
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 細胞内微小環境の差を認識しうる低分子化合物の創製に向けて2016

    • Author(s)
      高須清誠
    • Organizer
      京都市成長産業創造センター定期フォーラム
    • Place of Presentation
      京都市成長創造センター
    • Year and Date
      2016-08-04
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] 一つで二度おいしいタンデム触媒による有機合成2016

    • Author(s)
      高須清誠
    • Organizer
      グリーンケミストリーに根差した有機合成手法研究会
    • Place of Presentation
      名古屋工業大学
    • Year and Date
      2016-07-15
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Asymmetric Synthesis of Medium-Sized Ring Compounds via Short-Lived Cycloalkadiene Intermediates Based on Memory of Chirality Strategy2016

    • Author(s)
      Norihito Arichi, Tomohiro Ito, Ken-ichi Yamada, Yousuke Yamaoka, Kiyosei Takasu
    • Organizer
      Molecular Chirality Asia 2016
    • Place of Presentation
      Osaka
    • Year and Date
      2016-04-20
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Discovery of New Reactions and Utilities of 4-Membered Carbocyles2016

    • Author(s)
      Takasu, K.
    • Organizer
      Agora Bayer Symposium
    • Place of Presentation
      Kyoto
    • Year and Date
      2016-04-15
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Book] 薬学研究2017

    • Author(s)
      藤多哲朗、高須清誠
    • Total Pages
      170
    • Publisher
      東京化学同人
    • ISBN
      9784807917228
    • Related Report
      2017 Annual Research Report
  • [Book] くすりをつくる研究者の仕事2017

    • Author(s)
      高須清誠
    • Total Pages
      304
    • Publisher
      化学同人
    • ISBN
      9784759819311
    • Related Report
      2017 Annual Research Report

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Published: 2016-04-21   Modified: 2020-03-30  

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