• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Development of new transformation of polycyclic aromatic compounds utilizing reactive carbon-iodine(III) bond

Research Project

Project/Area Number 16K18854
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionMeijo University

Principal Investigator

Takenaga Naoko  名城大学, 薬学部, 助教 (60734845)

Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2018: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2017: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywordsヨウ素 / 芳香環 / 複素環 / 多環式 / 核酸塩基 / 有機ヨウ素
Outline of Final Research Achievements

We have developed the new metal-free coupling method of nucleobase derivatives such as purines toward nucleophiles (i.e. electron-rich arenes or amines), and facile synthesis of uracil-iodonium(III) salts as new attractive synthetic modules of these nucleobases. We have investigated in detail the optimized conditions for generating highly strained heterocyclic alkyne species from uracil-iodonium(III) salts with basic activation, which have led to development of the new vicinal functionalization of the uracil ring in a single synthetic operation.

Academic Significance and Societal Importance of the Research Achievements

核酸塩基のなかでも、ウラシル骨格は抗がん活性や抗ウイルス活性等を示す医薬品のファーマコアとして重要な機能を有しており、ウラシルのふたつの二重結合炭素を官能基化する手法を開発することは、創薬化学分野において重要である。本研究で開発したウラシルのビシナル官能基化法を用いると、合成難易度の高い複雑な芳香環化合物の骨格構築を高効率に行うことが可能であり、医薬品関連分子や機能性分子の創生研究への寄与につながりうる。

Report

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

    (25 results)

All 2019 2018 2017 2016

All Journal Article (8 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 8 results,  Open Access: 3 results,  Acknowledgement Compliant: 1 results) Presentation (17 results) (of which Int'l Joint Research: 2 results)

  • [Journal Article] Vicinal Functionalization of Uracil Heterocycles with Base Activation of Iodonium(III) Salts2019

    • Author(s)
      Takenaga Naoko、Ueda Shohei、Hayashi Takumi、Dohi Toshifumi、Kitagaki Shinji
    • Journal Title

      HETEROCYCLES

      Volume: 99 Issue: 2 Pages: 865-865

    • DOI

      10.3987/com-18-s(f)93

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Planar Chiral Phosphino[2.2]paracyclophanol-catalyzed Highly Regio- and Stereoselective [3+2] Annulation Reaction of Morita-Baylis-Hillman Carbonates with Dicyanomethylideneoxindoles2019

    • Author(s)
      Kitagaki Shinji、Tsuji Mayuka、Teramoto Hideki、Takenaga Naoko、Yoshida Keisuke
    • Journal Title

      HETEROCYCLES

      Volume: 印刷中 Issue: 1 Pages: 127-127

    • DOI

      10.3987/com-19-s(f)3

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Planar Chiral [2.2]Paracyclophane-Based Bisoxazoline Ligands: Design, Synthesis, and Use in Cu-Catalyzed Inter- and Intramolecular Asymmetric O–H Insertion Reactions2018

    • Author(s)
      Kitagaki Shinji、Murata Shunsuke、Asaoka Kisaki、Sugisaka Kenta、Mukai Chisato、Takenaga Naoko、Yoshida Keisuke
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 66 Issue: 10 Pages: 1006-1014

    • DOI

      10.1248/cpb.c18-00519

    • NAID

      130007490997

    • ISSN
      0009-2363, 1347-5223
    • Year and Date
      2018-10-01
    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Facile synthesis of stable uracil-iodonium(III) salts with various counterions.2018

    • Author(s)
      N. Takenaga, S. Ueda, T. Hayashi, T. Dohi, S. Kitagaki
    • Journal Title

      Heterocycles

      Volume: 97 Issue: 2 Pages: 1248-1248

    • DOI

      10.3987/com-18-s(t)80

    • Related Report
      2018 Annual Research Report 2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Planar chiral [2.2]paracyclophane-based phosphine-phenols: Use in enantioselective [3+2] annulations of allenoates and N-tosylimines.2018

    • Author(s)
      Shinji Kitagaki, Kento Nakamura, Chiharu Kawabata, Asuna Ishikawa, Naoko Takenaga, Keisuke Yoshida
    • Journal Title

      Org. Biomol. Chem.

      Volume: 16 Issue: 10 Pages: 1770-1778

    • DOI

      10.1039/c8ob00248g

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Atropisomeric chiral diiododienes, (Z,Z)-2,3-di(1-iodoalkylidene)tetralins: Synthesis, enantiomeric resolution, and application in asymmetric catalysis2017

    • Author(s)
      M. Ogasawara, H. Sasa, H. Hu, Y. Amano, H. Nakajima, N. Takenaga, K. Nakajima, Y. Kita, T. Takahashi, T. Dohi
    • Journal Title

      Org. Lett.

      Volume: 19 Issue: 15 Pages: 4102-4105

    • DOI

      10.1021/acs.orglett.7b01876

    • NAID

      120006556293

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Chiral Atropisomeric 8,8’-Diiodo binaphthalene for asymmetric dearomatizing spirolactonizations in hypervalent iodine oxidations2017

    • Author(s)
      T. Dohi, H. Sasa, K. Miyazaki, M. Fujitake, N. Takenaga, Y. Kita
    • Journal Title

      J. Org. Chem.

      Volume: 82 Issue: 22 Pages: 11954-11960

    • DOI

      10.1021/acs.joc.7b02037

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Planar Chiral [2.2]Paracyclophane-Based Phosphine-Phenol Catalysts: Application to the Aza-Morita-Baylis-Hillman Reaction of N -Sulfonated Imines with Various Vinyl Ketones2016

    • Author(s)
      Takenaga, N.; Adachi, S.; Furusawa, A.; Nakamura, K.; Suzuki, N.; Ohta, Y.; Komizu, M.; Mukai, C.; Kitagaki, S.
    • Journal Title

      Tetrahedron

      Volume: 72 Issue: 43 Pages: 6892-6897

    • DOI

      10.1016/j.tet.2016.09.023

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 安定かつ取扱い容易な核酸塩基ヨードニウム塩の開発2019

    • Author(s)
      武永尚子、上田祥平、林 巧実、土肥寿文、北垣伸治
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 環状歪みアルキンの発生を鍵とした核酸塩基の新規縮環反応の開発2019

    • Author(s)
      上田祥平、林 巧実、小林将太、武永尚子、土肥寿文
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] [2.2]パラシクロファン骨格を有する面不斉ホスフィン触媒を用いた[3+2]型環化反応2018

    • Author(s)
      北垣伸治、中村顕斗、川端千晴、舛中荘太、寺本英樹、辻真由香、吉田絵巳香、鷲野友亮、稲野真衣、武永尚子、吉田圭佑
    • Organizer
      第113回有機合成シンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] 核酸塩基の酸触媒カップリング法と新規合成素子の開発2018

    • Author(s)
      武永尚子、上田祥平、平井晶子、林 巧実、土肥寿文、北垣伸治
    • Organizer
      第7回JACI/GSCシンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] 面不斉ビスチオウレア分子が触媒する不斉Henry 反応における基質適用範囲の拡大検討2018

    • Author(s)
      服部友美、鈴木晶絵、小園友明、武永尚子、吉田圭佑、北垣伸治
    • Organizer
      第64回日本薬学会東海支部大会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 核酸塩基ヨードニウム塩の合成と新規環状アルキン等価体としての変換反応2018

    • Author(s)
      武永尚子、上田祥平、林 巧実、土肥寿文、北垣伸治
    • Organizer
      第68回日本薬学会 近畿支部 総会・大会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Synthesis and reactivity of stable uracil-iodonium(III) salts2018

    • Author(s)
      Shohei Ueda, Takumi Hayashi, Naoko Takenaga, Toshifumi Dohi, Shinji Kitagaki
    • Organizer
      Frontiers in Chemistry Armenia 2018
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] [2.2]パラシクロファン骨格を有する面不斉ホスフィン-フェノール触媒:アレンとメチレンインドリノンの[3+2]環化反応への適用2018

    • Author(s)
      吉田圭佑、舛中荘太、吉田絵巳香、鷲野友亮、稲野真衣、武永尚子、北垣伸治
    • Organizer
      第44回反応と合成の進歩シンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] 核酸塩基ヨードニウム塩の効率的合成と反応2018

    • Author(s)
      武永尚子、上田祥平、土肥寿文、北垣伸治
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Research-status Report
  • [Presentation] [2.2]パラシクロファンを基本骨格とする面不斉ビスチオウレア触媒を用いたニトロアルカンのニトロオレフィンへのMichael付加反応2017

    • Author(s)
      武永尚子、霜依莉子、深井凛太郎、北垣伸治
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台
    • Year and Date
      2017-03-25
    • Related Report
      2016 Research-status Report
  • [Presentation] [2.2]パラシクロファンを基本骨格とする面不斉ビスチオウレア触媒を用いたニトロアルドール反応の基質一般性の検討2017

    • Author(s)
      武永尚子、鈴木晶絵、小園友明、北垣伸治
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台
    • Year and Date
      2017-03-25
    • Related Report
      2016 Research-status Report
  • [Presentation] 核酸塩基の新規合成素子および効率的カップリング法の開発2017

    • Author(s)
      武永尚子、上田祥平、中山卓也、土肥寿文、北垣伸治
    • Organizer
      第112回有機合成シンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] スピロオキシインドール合成を志向したアレニルエステルの[3+2]環化反応への面不斉シクロファン含有ホスフィン触媒の適用2017

    • Author(s)
      舛中荘太、武永尚子、吉田圭佑、北垣伸治
    • Organizer
      第63回日本薬学会東海支部大会
    • Related Report
      2017 Research-status Report
  • [Presentation] スピロオキシインドール合成を志向したMBH付加体の[3+2]環化反応への面不斉シクロファン含有ホスフィン触媒の適用2017

    • Author(s)
      寺本英樹、武永尚子、吉田圭佑、北垣伸治
    • Organizer
      第63回日本薬学会東海支部大会
    • Related Report
      2017 Research-status Report
  • [Presentation] 面不斉シクロファン含有ホスフィン触媒によるイミンとアレンの[3+2]環化付加反応2017

    • Author(s)
      中村顕斗、川端千晴、石川明日菜、武永尚子、吉田圭佑、北垣伸治
    • Organizer
      第47回複素環化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] [2.2]パラシクロファン含有ホスフィン-フェノール触媒によるアレニルエステルの不斉[3+2]環化反応2016

    • Author(s)
      武永尚子、中村顕斗、川端千晴、兒玉直子、石川明日菜、安達早紀、北垣伸治
    • Organizer
      第46回複素環化学討論会
    • Place of Presentation
      金沢
    • Year and Date
      2016-09-26
    • Related Report
      2016 Research-status Report
  • [Presentation] Cyclophanylphosphine-catalyzed enantioselective [3+2] annulation of aldimine and allenoate2016

    • Author(s)
      Naoko Takenaga, Kento Nakamura, Chiharu Kawabata, Shinji Kitagaki
    • Organizer
      The 7th Nagoya/Nanjing/Shenyang Symposium of Pharmaceutical Sciences
    • Place of Presentation
      Nagoya
    • Year and Date
      2016-09-24
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research

URL: 

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

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi