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Establishment of novel synthetic strategy utilizing two types of photo-induced direct C(sp3)-H functionalization.

Research Project

Project/Area Number 26860009
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionThe University of Tokyo

Principal Investigator

NAGATOMO MASANORI  東京大学, 薬学研究科(研究院), 助教 (70634161)

Project Period (FY) 2014-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2015: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2014: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywords直截的変換反応 / 全合成 / 光化学反応 / 不斉アルキニル化反応 / ラクタシスチン / 20Sプロテアソーム阻害活性 / ザラゴジン酸C / 高脂血症治療薬 / 光反応 / C(sp3)-H直接官能基化 / フローリアクター / 発光ダイオード / オオムラリド / 青色発光ダイオード
Outline of Final Research Achievements

Development of direct transformations of C-H bonds has attracted intense attention from chemical community. We particularly focus on C(sp3)-H bond oxidations and functionalizations of multiply substituted carboskeletons.
This time we have achieved the following three research results.  1) Enantioselective alkynylation of C(sp3)-H bonds adjacent to a nitrogen atom has been achieved using only chiral p-tolyl tert-butyldimethylsilylethynyl sulfoximine and benzophenone under photo-irradiation conditions. 2) Total synthesis of (+)-lactacystin, a potent inhibitor of the 20S proteasome has been achieved using the chemo- and stereoselective photoinduced intermolecular C(sp3)-H alkynylation and intramolecular C(sp3)-H acylation. 3) Total synthesis of (+)-zaragozic acid C, having inhibitory activity of mammalian squalene synthase, has been achieved using the chemo- and stereoselective photoinduced intramolecular C(sp3)-H acylation.

Report

(3 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • Research Products

    (33 results)

All 2016 2015 2014 Other

All Journal Article (10 results) (of which Peer Reviewed: 10 results,  Open Access: 4 results,  Acknowledgement Compliant: 8 results) Presentation (19 results) (of which Int'l Joint Research: 3 results) Book (1 results) Remarks (3 results)

  • [Journal Article] Symmetry-Driven Strategy for the Assembly of the Core Tetracycle of (+)-Ryanodine: Synthetic Utility of a Cobalt-Catalyzed Olefin Oxidation and α-Alkoxy Bridgehead Radical Reaction2016

    • Author(s)
      M. Nagatomo, K. Hagiwara, K. Masuda, M. Koshimizu, T. Kawamata, Y. Matsui, D. Urabe, M. Inoue
    • Journal Title

      Chem. Eur. J.

      Volume: 22 Issue: 1 Pages: 222-229

    • DOI

      10.1002/chem.201503640

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Asymmetric Total Synthesis of (+)-Ryanodol and (+)-Ryanodine2016

    • Author(s)
      K. Masuda, M. Koshimizu, M. Nagatomo, M. Inoue
    • Journal Title

      Chem. Eur. J.

      Volume: 22 Issue: 1 Pages: 230-236

    • DOI

      10.1002/chem.201503641

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Unified Total Synthesis of 3-epi-Ryanodol, Cinnzeylanol, Cinncassiols A and B, and Structural Revision of Natural Ryanodol and Cinnacasol2016

    • Author(s)
      M. Koshimizu, M. Nagatomo, M. Inoue
    • Journal Title

      Angew. Chem., Int. Ed.

      Volume: 55 Issue: 7 Pages: 2493-2497

    • DOI

      10.1002/anie.201511116

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Chemical Conversion of Ryanodol to Ryanodine2016

    • Author(s)
      Kengo Masuda, Masanori Nagatomo, Masayuki Inoue
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 64 Issue: 7 Pages: 874-879

    • DOI

      10.1248/cpb.c16-00214

    • NAID

      130005160047

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Et3B-mediated Two- and Three-component Coupling Reactions via Radical Decarbonylation of α-Alkoxyacyl Tellurides: Single-step Construction of Densely Oxygenated Carboskeletons2015

    • Author(s)
      M. Nagatomo, D. Kamimura, Y. Matsui, K. Masuda, M. Inoue
    • Journal Title

      Chem. Sci.

      Volume: 6 Issue: 5 Pages: 2765-276

    • DOI

      10.1039/c5sc00457h

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Enantioselective Radical Alkynylation of C(sp3)-H Bonds Using Sulfoximine as a Traceless Chiral Auxiliary2015

    • Author(s)
      M. Nagatomo, S. Yoshioka, M. Inoue
    • Journal Title

      Chemistry - An Asian Journal

      Volume: 10 Issue: 1 Pages: 120-123

    • DOI

      10.1002/asia.201402983

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Decarbonylative Radical Coupling of α-Aminoacyl Tellurides: Single-Step Preparation of γ-Amino and α,β-Diamino Acids and Rapid Synthesis of Gabapentin and Manzacidin A2015

    • Author(s)
      M. Nagatomo, H. Nishiyama, H. Fujino, M. Inoue
    • Journal Title

      Angew. Chem., Int. Ed.

      Volume: 54 Issue: 5 Pages: 1537-1541

    • DOI

      10.1002/anie.201410186

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Application of Two Direct C(sp3)-H Functionalizations for Total Synthesis of (+)-Lactacystin2015

    • Author(s)
      S. Yoshioka, M. Nagatomo, M. Inoue
    • Journal Title

      Organic Letter

      Volume: 17 Issue: 1 Pages: 90-93

    • DOI

      10.1021/ol503291s

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Total Synthesis of Ryanodol2014

    • Author(s)
      Masanori Nagatomo, Masaki Koshimizu, Kengo Masuda, Toshiki Tabuchi, Daisuke Urabe, Masayuki Inoue
    • Journal Title

      Journal of the American Chemical Society

      Volume: 136 Issue: 16 Pages: 5916-5919

    • DOI

      10.1021/ja502770n

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Photochemically Induced Radical Alkenylation of C(sp3)-H Bonds2014

    • Author(s)
      Y. Amaoka, M. Nagatomo, M. Watanabe, K. Tao, S. Kamijo, M. Inoue
    • Journal Title

      Chem. Sci.

      Volume: 5 Issue: 11 Pages: 4339-4345

    • DOI

      10.1039/c4sc01631a

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Presentation] クラジェリン類の合成研究2016

    • Author(s)
      増田圭佑、長友優典、井上将行
    • Organizer
      日本薬学会 第136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県・横浜市)
    • Year and Date
      2016-03-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] 分子間ラジカル付加反応を鍵とするタキサンジテルペンの収束的合成研究2016

    • Author(s)
      吉岡駿、長友優典、井上将行
    • Organizer
      日本薬学会 第136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県・横浜市)
    • Year and Date
      2016-03-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] 立体選択的ラジカル付加反応を鍵とするタキソールの合成研究2016

    • Author(s)
      的場博亮、長友優典、井上将行
    • Organizer
      日本薬学会 第136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県・横浜市)
    • Year and Date
      2016-03-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] 高酸化度化合物の合成を指向したラジカル-極性交差型連結反応の開発2016

    • Author(s)
      松井勇樹、長友優典、井上将行
    • Organizer
      日本薬学会 第136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県・横浜市)
    • Year and Date
      2016-03-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] Unified Total Synthesis of Ryanoids2015

    • Author(s)
      Masaki Koshimizu, Masanori Nagatomo, Masayuki Inoue
    • Organizer
      pacifichem2015
    • Place of Presentation
      USA/Honolulu
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] A-315675およびその類縁対の収束的合成戦略の開発2015

    • Author(s)
      澤田英之、長友優典、井上将行
    • Organizer
      第70回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      長岡工業高等専門学校(新潟県・長岡市)
    • Year and Date
      2015-11-21
    • Related Report
      2015 Annual Research Report
  • [Presentation] ポリオキシン類の収束的全合成2015

    • Author(s)
      藤野遥、長友優典、井上将行
    • Organizer
      第108回有機合成シンポジウム
    • Place of Presentation
      早稲田大学国際会議場(東京都・新宿区)
    • Year and Date
      2015-11-05
    • Related Report
      2015 Annual Research Report
  • [Presentation] Asymmetric Total Synthesis of (+)-Ryanodol and (+)-Ryanodine2015

    • Author(s)
      Masanori Nagatomo, Kengo Masuda, Masaki Koshimizu, Masayuki Inoue
    • Organizer
      ICCEOCA-10
    • Place of Presentation
      台湾/高雄市
    • Year and Date
      2015-11-02
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthetic Study of Cladiellin D2015

    • Author(s)
      Keisuke Masuda, Masanori Nagatomo, Masayuki Inoue
    • Organizer
      LMU-UTOKYO SYMPOSIUM 2015
    • Place of Presentation
      Germany/Munich
    • Year and Date
      2015-10-27
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] リアノイド類の網羅的全合成2015

    • Author(s)
      小清水正樹、長友優典、井上将行
    • Organizer
      第57回天然有機化合物討論会
    • Place of Presentation
      神奈川県民ホール(神奈川県・横浜市)
    • Year and Date
      2015-09-09
    • Related Report
      2015 Annual Research Report
  • [Presentation] ザラゴジン酸Cの合成研究2015

    • Author(s)
      川俣貴裕、長友優典、井上将行
    • Organizer
      第50回天然物化学談話会
    • Place of Presentation
      グリーンピア岩沼モンタナリゾート(宮城県・岩沼市)
    • Year and Date
      2015-07-01
    • Related Report
      2015 Annual Research Report
  • [Presentation] C(sp3)-H直接官能基化を鍵とするラクタシスチンの全合成2015

    • Author(s)
      吉岡駿, 長友優典, 井上将行
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸学院大学
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] C(sp3)-H結合のアシル化反応を利用するザラゴジン酸Cの新合成戦略2015

    • Author(s)
      川俣貴裕, 長友優典, 井上将行
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸学院大学
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] 脱カルボニル化を伴う3成分ラジカル-極性交差型反応の開発2014

    • Author(s)
      松井勇樹, 上村大護, 松村祥子, 長友優典, 井上将行
    • Organizer
      第68回有合協関東支部シンポ
    • Place of Presentation
      新潟大学五十嵐キャンパス
    • Year and Date
      2014-11-29 – 2014-11-30
    • Related Report
      2014 Research-status Report
  • [Presentation] (+)-リアノジンの不斉全合成2014

    • Author(s)
      枡田健吾, 長友優典, 小清水正樹, 萩原幸司, 田渕俊樹, 占部大介, 井上将行
    • Organizer
      第56回天然有機化合物討論会
    • Place of Presentation
      高知県民文化ホール
    • Year and Date
      2014-10-15 – 2014-10-17
    • Related Report
      2014 Research-status Report
  • [Presentation] α-アミノ炭素ラジカルを用いたマンザシジンAの全合成2014

    • Author(s)
      藤野 遥, 長友優典, 井上将行
    • Organizer
      第31回有機合成化学セミナー
    • Place of Presentation
      休暇村 志賀島(福岡県福岡市東区大字勝馬)
    • Year and Date
      2014-09-17 – 2014-09-19
    • Related Report
      2014 Research-status Report
  • [Presentation] リアノドールの全合成2014

    • Author(s)
      小清水正樹, 長友優典, 枡田健吾, 萩原幸司, 田渕俊樹, 占部大介, 井上将行
    • Organizer
      第31回有機合成化学セミナー
    • Place of Presentation
      休暇村 志賀島(福岡県福岡市東区大字勝馬)
    • Year and Date
      2014-09-17 – 2014-09-19
    • Related Report
      2014 Research-status Report
  • [Presentation] (±)-リアノドールの全合成2014

    • Author(s)
      小清水正樹, 長友優典, 枡田健吾, 田渕俊樹, 占部大介, 井上将行
    • Organizer
      第12回次世代を担う有機化学シンポジウム
    • Place of Presentation
      日本薬学会長井記念ホール
    • Year and Date
      2014-05-23 – 2014-05-24
    • Related Report
      2014 Research-status Report
  • [Presentation] α-アザ炭素ラジカルを用いたマンザシジンの合成研究2014

    • Author(s)
      藤野遥, 西山勇人, 長友優典, 井上将行
    • Organizer
      第67回有合協関東支部シンポジウム
    • Place of Presentation
      慶應義塾大学矢上キャンパス
    • Year and Date
      2014-05-17
    • Related Report
      2014 Research-status Report
  • [Book] 月刊化学4月号「リアノジン類の統一的全合成-多様性を志向した共通中間体の設計戦略」2016

    • Author(s)
      長友優典、井上将行
    • Total Pages
      2
    • Publisher
      化学同人
    • Related Report
      2015 Annual Research Report
  • [Remarks] 東京大学大学院薬学系研究科有機反応化学教室ホームページ

    • URL

      http://www.f.u-tokyo.ac.jp/~inoue/index.html

    • Related Report
      2015 Annual Research Report
  • [Remarks] 東京大学大学院薬学系研究科ホームページ

    • URL

      http://www.f.u-tokyo.ac.jp/

    • Related Report
      2015 Annual Research Report
  • [Remarks] 東京大学大学院薬学系研究科 有機反応化学教室ホームページ

    • URL

      http://www.f.u-tokyo.ac.jp/~inoue/index.html

    • Related Report
      2014 Research-status Report

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Published: 2014-04-04   Modified: 2017-05-10  

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