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2009 Fiscal Year Final Research Report

Development of highly atom-economical synthetic methods based on catalytic cascade reactions

Research Project

  • PDF
Project/Area Number 19689001
Research Category

Grant-in-Aid for Young Scientists (A)

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

Principal Investigator

OHNO Hiroaki  Kyoto University, 薬学研究科, 准教授 (30322192)

Project Period (FY) 2007 – 2009
Keywords有機化学
Research Abstract

The author investigated development of synthetic methods based on catalytic cascade of atom-economical reactions such as C-H bond activation and multi-component reactions. Consequently, several methods for construction of fused heterocycles such as indoles, isoquinolines, isoindoles, carbazoles, and quinazolines have been developed. Furthermore, total syntheses of ergot alkaloids and jaspine B, as well as efficient synthesis of trifluoromethylalkene dipeptide isosteres have been achieved. These results provide a preliminary model for efficient organic synthesis.

  • Research Products

    (40 results)

All 2010 2009 2008 2007 Other

All Journal Article (23 results) (of which Peer Reviewed: 23 results) Presentation (15 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Direct Synthesis of Quinazolines through Copper-Catalyzed Reaction of Aniline-Derived Benzamidines.2010

    • Author(s)
      Y.Ohta, Y.Tokimizu, S.Oishi, N.Fujii, H.Ohno.
    • Journal Title

      Org.Lett 12(17)

      Pages: 3963-3965

    • Peer Reviewed
  • [Journal Article] Stereoselective Divergent Synthesis of Four Diastereomers of Pachastrissamine (Jaspine B).2010

    • Author(s)
      Y.Yoshimitsu, S.Inuki, S.Oishi, N.Fujii, H.Ohno.
    • Journal Title

      J.Org.Chem. 75(11)

      Pages: 3843-3846

    • Peer Reviewed
  • [Journal Article] Ring-Construction/Stereoselective Functionalization Cascade: Total Synthesis of Pachastrissamine (Jaspine B) through Palladium-Catalyzed Bis-cyclization of Propargyl Chlorides and Carbonates.2010

    • Author(s)
      S.Inuki, Y.Yoshimitsu, S.Oishi, N.Fujii, H.Ohno.
    • Journal Title

      J.Org.Chem. 75(11)

      Pages: 3831-3842

    • Peer Reviewed
  • [Journal Article] Construction of Linked Nitrogen Heterocycles by Palladium(0)-Catalyzed Intramolecular Domino Cyclization of 2-Alkynylaziridines Bearing a 2-Aminoethyl Group via Ring Expansion with Isocyanate2010

    • Author(s)
      A.Okano, S.Oishi, T.Tanaka, N.Fujii, H.Ohno.
    • Journal Title

      J.Org.Chem. 75(10)

      Pages: 3396-3400

    • Peer Reviewed
  • [Journal Article] Synthesis of Fused and Linked Bicyclic Nitrogen Heterocycles by Palladium-Catalyzed Domino Cyclization of Propargyl Bromide.2010

    • Author(s)
      A.Okano, K.Tsukamoto, S.Kosaka, H.Maeda, S.Oishi, T.Tanaka, N.Fujii, H.Ohno.
    • Journal Title

      Chem.Eur.J. 16(28)

      Pages: 8410-8418

    • Peer Reviewed
  • [Journal Article] Gold-Catalyzed Intramolecular Alkyne Cycloisomerization Cascade: Direct Synthesis of Aryl-Annulated[ a]carbazoles from Aniline-Substituted Diethynylarenes.2010

    • Author(s)
      K.Hirano, Y.Inaba, T.Watanabe, S.Oishi, N.Fujii, H.Ohno.
    • Journal Title

      Adv.Synth.Catal. 352(2)

      Pages: 368-372

    • Peer Reviewed
  • [Journal Article] Efficient Synthesis of Pyrimido[1,2-c][1,3]- benzothiazin-6-imines and Related Tricyclic Heterocycles by SNAr-Type C-S, C-N, or C-O Bond Formation with Heterocumulenes.2010

    • Author(s)
      T.Mizuhara, S.Oishi, N.Fujii, H.Ohno.
    • Journal Title

      J.Org.Chem. 75(1)

      Pages: 265-268

    • Peer Reviewed
  • [Journal Article] Ring-Construction/Stereoselective Functionalization Cascade: Total Synthesis of Pachastrissamine (Jaspine B) through Palladium-Catalyzed Bis-cyclization of Bromoallenes.2009

    • Author(s)
      S.Inuki, Y.Yoshimitsu, S.Oishi, N.Fujii, H.Ohno.
    • Journal Title

      Org.Lett. 11(19)

      Pages: 4478-4481

    • Peer Reviewed
  • [Journal Article] Construction of Nitrogen Heterocycles Bearing an Aminomethyl Group by Copper-Catalyzed Domino Three-Component Coupling-Cyclization2009

    • Author(s)
      Y.Ohta, H.Chiba, S.Oishi, N.Fujii, H.Ohno.
    • Journal Title

      J.Org.Chem. 74(18)

      Pages: 7052-7058

    • Peer Reviewed
  • [Journal Article] Rapid Access to 3-(Aminomethyl)isoquinoline-Fused Polycyclic Compounds by Copper-Catalyzed Four-Component Coupling, Cascade Cyclisation and Oxidation.2009

    • Author(s)
      Y.Ohta, Y.Kubota, T.Watabe, H.Chiba, S.Oishi, N.Fujii, H.Ohno.
    • Journal Title

      J.Org.Chem. 74(16)

      Pages: 6299-6302

    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Direct Synthesis of Carbazoles via One-Pot N-Arylation and Oxidative Biaryl Coupling: Synthesis and Mechanistic Study.2009

    • Author(s)
      T.Watanabe, S.Oishi, N.Fujii, H.Ohno.
    • Journal Title

      J.Org.Chem. 74(13)

      Pages: 4720-4726

    • Peer Reviewed
  • [Journal Article] Facile Synthesis of 1,2,3,4-Tetrahydro-β-carbolines by One-Pot Domino Three-Component Indole Formation and Nucleophilic Cyclization.2009

    • Author(s)
      Y.Ohta, S.Oishi, N.Fujii, H.Ohno.
    • Journal Title

      Org.Lett. 11(9)

      Pages: 1979-1982

    • Peer Reviewed
  • [Journal Article] Total Synthesis of (±)-Lysergic Acid, Lysergol, and Isolysergol by Palladium-Catalyzed Domino Cyclization of Amino Allenes Bearing a Bromoindolyl Group.2008

    • Author(s)
      S.Inuki, S.Oishi, N.Fujii, H.Ohno.
    • Journal Title

      Org.Lett 10(22)

      Pages: 5239-5242

    • Peer Reviewed
  • [Journal Article] Concise Synthesis of Indole-Fused 1,4-Diazepines through Copper(I)-Catalyzed Domino Three-Component Coupling-Cyclization-N-Arylation under Microwave Irradiation.2008

    • Author(s)
      Y.Ohta, H.Chiba, S.Oishi, N.Fujii, H.Ohno.
    • Journal Title

      Org.Lett. 10(16)

      Pages: 3535-3538

    • Peer Reviewed
  • [Journal Article] N.Fujii.Palladium-Catalysed Biscyclisation of Allenic Bromoalkenes through Zipper-Mode Cascade.2008

    • Author(s)
      A.Okano, T.Mizutani, S.Oishi, T.Tanaka, H.Ohno
    • Journal Title

      Chem.Commun 30

      Pages: 3534-3536

    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed sp^3 C-H Activation of Simple Alkyl Groups: Direct Preparation of Indoline Derivatives from N-Alkyl-2-bromoanilines.2008

    • Author(s)
      T.Watanabe, S.Oishi, N.Fujii, H.Ohno.
    • Journal Title

      Org.Lett 10(9)

      Pages: 1759-1762

    • Peer Reviewed
  • [Journal Article] Direct Construction of Bicyclic Heterocycles by Palladium-Catalyzed Tandem Cyclization of Propargyl Bromides.2008

    • Author(s)
      H.Ohno, A.Okano, S.Kosaka, K.Tsukamoto, M.Ohata, K.Ishihara, H.Maeda, T.Tanaka, N.Fujii.
    • Journal Title

      Org.Lett 10(6)

      Pages: 1171-1174

    • Peer Reviewed
  • [Journal Article] Facile Synthesis of 3-(Aminomethyl)isoquinoline by Copper-Catalysed Domino Four-Component Coupling and Cyclisation.2008

    • Author(s)
      Y.Ohta, S.Oishi, N.Fujii, H.Ohno.
    • Journal Title

      Chem.Commun 7

      Pages: 835-837

    • Peer Reviewed
  • [Journal Article] Gold-Catalyzed Hydroarylation of Allenes: A Highly Regioselective Carbon-Carbon Bond Formation Producing Six-Membered Rings.2007

    • Author(s)
      T.Watanabe, S.Oishi, N.Fujii, H.Ohno.
    • Journal Title

      Org.Lett 9(23)

      Pages: 4821-4824

    • Peer Reviewed
  • [Journal Article] Zipper-Mode Double C-H Activation: Palladium-Catalyzed Direct Construction of Highly-Fused Heterocyclic Systems.2007

    • Author(s)
      H.Ohno, M.Iuchi, N.Fujii, T.Tanaka.
    • Journal Title

      Org.Lett 9(23)

      Pages: 4813-4815

    • Peer Reviewed
  • [Journal Article] One-Pot Synthesis of Carbazoles by Palladium-Catalyzed N-Arylation and Oxidative Coupling.2007

    • Author(s)
      T.Watanabe, S.Ueda, S.Inuki, S.Oishi, N.Fujii, H.Ohno.
    • Journal Title

      Chem.Commun. 43

      Pages: 4516-4518

    • Peer Reviewed
  • [Journal Article] Heck-Type Cyclization of Oxime Ethers: Stereoselective Carbon-Carbon Bond Formation with Aryl Halides to Produce Heterocyclic Oximes2007

    • Author(s)
      H.Ohno, A.Aso, Y.Kadoh, N.Fujii, T.Tanaka
    • Journal Title

      Angew.Chem.Int.Ed. 46(33)

      Pages: 6325-6328

    • Peer Reviewed
  • [Journal Article] N.Fujii.Efficient Synthesis of Trifluoromethyl and Related Trisubstituted Alkene Dipeptide Isosteres by Palladium-catalyzed Carbonylation of Amino Acid-derived Allylic Carbonates.

    • Author(s)
      E.Inokuchi, T.Narumi, A.Niida, K.Kobayashi, K.Tomita, S.Oishi, H.Ohno
    • Journal Title

      J.Org.Chem.

    • Peer Reviewed
  • [Presentation] 金触媒を用いたアニリン誘導体の分子内連続環化反応による芳香環縮環型カルバゾール誘導体の合成2010

    • Author(s)
      稲葉祐介、大野浩章、他
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-28
  • [Presentation] 銅触媒による多成分カップリング反応を用いたワンポット含窒素多環式複素環骨格構築法の開発2009

    • Author(s)
      太田悠介、大野浩章、他
    • Organizer
      第35回反応と合成の進歩シンポジウム
    • Place of Presentation
      金沢
    • Year and Date
      2009-11-16
  • [Presentation] 多成分カップリング・連続環化反応によるピロロインドール誘導体及びジピロロピリジン誘導体の合成研究2009

    • Author(s)
      鈴木大和、大野浩章、他
    • Organizer
      第7回次世代を担う有機化学シンポジウム
    • Place of Presentation
      大阪
    • Year and Date
      2009-07-24
  • [Presentation] Pd触媒によるアレン連続環化反応を利用したErgotAlkaloid骨格の一挙構築法開発と応用2008

    • Author(s)
      井貫晋輔、大野浩章、他
    • Organizer
      第34回反応と合成の進歩シンポジウム
    • Place of Presentation
      京都
    • Year and Date
      2008-11-24
  • [Presentation] 銅触媒-マイクロ波照射を用いた連続三成分カップリング-環化-N-アリール化反応によるインドール縮環型1,4-ジアゼピン合成法開発2008

    • Author(s)
      太田悠介、大野浩章、他
    • Organizer
      第34回反応と合成の進歩シンポジウム
    • Place of Presentation
      京都
    • Year and Date
      2008-11-04
  • [Presentation] 触媒的連続結合形成反応の開発とErgotアルカロイド全合成への応用2008

    • Author(s)
      大野浩章
    • Organizer
      第43回天然物化学討論会
    • Place of Presentation
      大阪
    • Year and Date
      2008-07-10
  • [Presentation] パラジウム触媒を用いたアレン連続環化反応を利用したErgot Alkaloid 骨格の一挙構築法開発と応用2008

    • Author(s)
      井貫晋輔、大野浩章、他
    • Organizer
      第6回次世代を担う有機化学シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2008-05-30
  • [Presentation] Pd触媒によるアレン連続環化反応を利用したErgotAlkaloid骨格の一挙構築法開発と応用2008

    • Author(s)
      井貫晋輔、大野浩章、他
    • Organizer
      第6回次世代を担う有機化学シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2008-05-30
  • [Presentation] パラジウム触媒を用いたプロパルギルブロミドの連続的閉環反応による二環性複素環の一挙構築2007

    • Author(s)
      岡野晃典、大野浩章、他
    • Organizer
      第33回反応と合成の進歩シンポジウム
    • Place of Presentation
      長崎
    • Year and Date
      20071105-20071106
  • [Presentation] Construction of 2-(aminomethyl)indole motif by Cu-catalyzed multicomponent reaction2007

    • Author(s)
      Yusuke Ohta, Hiroaki Ohno, et al.
    • Organizer
      234th ACS meeting & exposition
    • Place of Presentation
      ボストン
    • Year and Date
      20070819-20070823
  • [Presentation] Construction of 2-(aminomethyl)indole motif by Cu-catalyzed multi-component reaction2007

    • Author(s)
      Yusuke Ohta, Hiroaki Ohno, et al.
    • Organizer
      14th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
    • Place of Presentation
      奈良
    • Year and Date
      20070802-20070806
  • [Presentation] Synthesis and application of carbazoles by palladium-catalyzed tandem N-arylation of carbazoles by palladium-catalyzed tandem N-arylation and oxidative C-H activation2007

    • Author(s)
      Toshiaki Watanabe, Hiroaki Ohno, et al.
    • Organizer
      14th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
    • Place of Presentation
      奈良
    • Year and Date
      20070802-20070806
  • [Presentation] Synthesis and application of carbazoles by palladium-catalyzed tandem N-arylation and oxidative C-H activation2007

    • Author(s)
      Toshiaki Watanabe, Hiroaki Ohno, et al.
    • Organizer
      Eighth Tetrahedron Symposium
    • Place of Presentation
      ベルリン
    • Year and Date
      20070626-20090629
  • [Presentation] Pd触媒を用いたタンデム型N-アリール化-C-H 活性化によるカルバゾールの合成と反応機構の考察2007

    • Author(s)
      渡部敏明、大野浩章、他
    • Organizer
      第5回次世代を担う有機化学シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      20070525-20070526
  • [Presentation] 連続結合形成反応による縮環型芳香族化合物の一挙合成法の開発2007

    • Author(s)
      大野浩章、他
    • Organizer
      第33回反応と合成の進歩シンポジウム
    • Place of Presentation
      長崎
    • Year and Date
      2007-11-06
  • [Remarks] ホームページ等

    • URL

      http://www.pharm.kyoto-u.ac.jp/seizo/home.htm

  • [Patent(Industrial Property Rights)] Eg5阻害剤2008

    • Inventor(s)
      藤井信孝、大石真也、大野浩章、他
    • Industrial Property Rights Holder
      京都大学・ファルマIP
    • Industrial Property Number
      特許,特願2008-331963
    • Filing Date
      2008-12-26

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Published: 2012-02-13   Modified: 2016-04-21  

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