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Synthetic studies on polycyclic alkaloids through carbamoyl metal complexes.

Research Project

Project/Area Number 20790008
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

YASUI Yoshizumi  Tohoku University, 原子分子材料科学高等研究機構, 助教 (10432410)

Project Period (FY) 2008 – 2009
Project Status Completed (Fiscal Year 2009)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2009: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2008: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords天然物合成 / 金属触媒反応 / アミド化 / アルカロイド / 不斉反応 / パラジウム触媒反応 / ラクタム形成法 / エナンチオ選択的反応 / シアノアミド化反応 / 連続反応 / アルカロイド合成 / オキシインドール / 遷移金属反応 / カルバモイル金属錯体
Research Abstract

Since polycyclic alkaloids are known to exhibit a broad range of important bioactivities, synthetic study of this class of compounds is an important task from pharmaceutical point of view. In this project, we studied a new method to approach polycyclic alkaloids by using carbamoyl metal complexes. As a result, lactam formation reaction starting from chloroformamides and cyanoformamides having olefin has been developed, and was applied to the syntheses of polycyclic alkaloids.

Report

(3 results)
  • 2009 Annual Research Report   Final Research Report ( PDF )
  • 2008 Annual Research Report
  • Research Products

    (32 results)

All 2010 2009 2008

All Journal Article (17 results) (of which Peer Reviewed: 17 results) Presentation (15 results)

  • [Journal Article] Preparation of・, ・-Unsaturated Lactams through Intramolecular Electrophilic Carbamoylation of Alkenes.2009

    • Author(s)
      Y. Yasui, I. Kakinokihara, H. Takeda, Y. Takemoto
    • Journal Title

      Synthesis 23

      Pages: 3989-3993

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Pd-catalyzed Intramolecular Amidation of 2-(Buta-1, 3-dienyl)phenylcarbamoyl Chloride: a Concise Synthesis of Spiro[indoline-3, 3'-pyrrolidine].2009

    • Author(s)
      H. Kamisaki, Y. Yasui, Y. Takemoto
    • Journal Title

      Tetrahedron Lett. 50(21)

      Pages: 2589-2592

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthetic Studies on Vincorine: Access to the 3a, 8a-Dialkyl-1, 2, 3, 3a, 8, 8a-hexahydropyrrolo[2, 3-b]indole Skeleton.2009

    • Author(s)
      Y. Yasui, T. Kinugawa, Y. Takemoto
    • Journal Title

      Chem. Commun 28

      Pages: 4275-4277

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthetic studies on vincorine : access to the 3a,8a-dialkyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole skeleton2009

    • Author(s)
      Y.Yasui, T.Kinugawa, Y.Takemoto
    • Journal Title

      Chem.Commun.

      Pages: 4275-4277

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Gold(I)-Catalyzed Tandem Reactions Initiated by Hydroamination of Alkynyl Carbamates : Application to the Synthesis of Nitidine2009

    • Author(s)
      T.Enomoto, A.-L.Girard, Y.Yasui, Y.Takemoto
    • Journal Title

      J.Org.Chem. 74

      Pages: 9158-9164

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis, X-ray crystal structures, and computational studies of 1,1'-bridged 4,4'-diaryl-2,2'-bibenzimidazoles : building blocks for supramolecular structures2009

    • Author(s)
      D.K.Frantz, A.A.Sullivan, Y.Yasui, A.Linden, K.K.Baldridge, J.S.Siegel
    • Journal Title

      Org.Biomol.Chem. 7

      Pages: 2347-2352

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Preparation of α,β-Unsaturated Lactams through Intramolecular Electrophilic Carbamoylation of Alkenes2009

    • Author(s)
      Y.Yasui, I.Kakinokihara, H.Takeda, Y.Takemoto
    • Journal Title

      Synthesis

      Pages: 3989-3993

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] First Total Synthesis of(+)-11-Hydroxyerythratidine2009

    • Author(s)
      T.Onoda, Y.Takikawa, T.Fujimoto, Y.Yasui, K.Suzuki, T.Matsumoto
    • Journal Title

      Synlett

      Pages: 1041-1046

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Pd-catalyzed intramolecular amidation of 2-(buta-1,3-dienyl)phenylcarbamoyl chloride : a concise synthesis of spiro[indoline-3,3'-pyrrolidine]2009

    • Author(s)
      H.Kamisaki, Y.Yasui, Y.Takemoto
    • Journal Title

      Tetrahedron Lett. 50

      Pages: 2589-2592

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Y. Yasui, H. Takeda, Y. Takemoto2008

    • Author(s)
      Toward General Access to the Aspidosperma-Type Terpenoid Indole Alkaloids: Synthesis of the Key 3, 3-Disubstituted Piperidones through Enantioselective Intramolecular Heck-Type Reaction of Chloroformamides.
    • Journal Title

      Chem. Pharm. Bull. 56(11)

      Pages: 1567-1574

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Synthesis of 3, 3-Disubstituted Oxindoles through Pd-Catalyzed Cyanoamidation.2008

    • Author(s)
      Y. Yasui, H. Kamisaki, Y. Takemoto
    • Journal Title

      Org. Lett. 10(15)

      Pages: 3303-3306

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Intra- and Intermolecular Amidation of C-C Unsaturated Bonds through Palladium-Catalyzed Reactions of Carbamoyl Derivatives.2008

    • Author(s)
      Y. Yasui, Y. Takemoto
    • Journal Title

      Chem. Rec. 8(6)

      Pages: 386-394

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Toward General Access to the Aspidosperma-Type Terpenoid Indole Alkaloids : Synthesis of the Key 3,3-Disubstituted Piperidones through Enantioselective Intramolecular Heck-Type Reaction of Chloroformamides2008

    • Author(s)
      Yoshizumi YASUI, Hiroshi TAKEDA, Yoshiji TAKEMOTO
    • Journal Title

      Chem. Pharm. Bull 56

      Pages: 1567-1574

    • NAID

      110006968058

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Intra-and Intermolecular Amidation of C-C Unsaturated Bonds Through Palladium-Catalyzed Reactions of Carbamoyl Derivatives2008

    • Author(s)
      YOSHIZUMI YASUI, YOSHIJI TAKEMOTO
    • Journal Title

      The Chemical Record 8

      Pages: 386-394

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Concise Synthesis of the CDE Ring System of Tetrahydroisoquinoline Alkaloids Using Carbophilic Lewis Acid-Catalyzed Hydroamidation and Oxidative Friedel-Crafts Cyclization2008

    • Author(s)
      Shingo Obika, Yoshizumi Yasui, Reiko Yanada, Yoshiji Takemotc
    • Journal Title

      J. Org. Chem 73

      Pages: 5206-5209

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Synthesis of 3,3-Disubstituted Oxindoles through Pd-Catalyzed Cyanoamidation2008

    • Author(s)
      Yoshizumi Yasui, Haruhi Kamisaki, and Yoshiji Takemoto
    • Journal Title

      Org. Lett 10

      Pages: 3303-3306

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Synthesis of 3,3-Disubstituted Oxindoles through Pd-Ca talyzed Cyanoamidation2008

    • Author(s)
      Taro Enomoto, Shingo Obika, Yo shizumi Yasui, Yoshiji Takemoto
    • Journal Title

      Synlett 2008

      Pages: 1647-1650

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] ヘリセン部位を有する光学活性シアニンの合成2010

    • Author(s)
      安井義純、原口信宏、山口雅彦
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] Synthesis of Chiral Cyanines Containing Helicene2009

    • Author(s)
      安井義純, 原口信宏, 山口雅彦
    • Organizer
      the Sixth International Forum on Chemistry of Functional Organic Chemicals(IFOC-6)
    • Place of Presentation
      東京
    • Year and Date
      2009-11-16
    • Related Report
      2009 Annual Research Report
  • [Presentation] Construction of optically active molecular sheets : synthesis and aggregation of cyclic helicene trimer containing 2,6-diamidopyridine moiety2009

    • Author(s)
      安井義純, 山口雅彦
    • Organizer
      Tateshina Conference on Organic Chemistry
    • Place of Presentation
      蓼科
    • Year and Date
      2009-11-14
    • Related Report
      2009 Annual Research Report
  • [Presentation] Pd-Catalyzed Intramolecular Amidination of Unsaturated Isothioureas: A Concise Synthesis of Indolo[2, 3-b]quinolines.2009

    • Author(s)
      H. Takeda, Y. Yasui, Y. Takemoto
    • Organizer
      15th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-15)
    • Place of Presentation
      Glasgow, UK
    • Year and Date
      2009-07-27
    • Related Report
      2009 Final Research Report
  • [Presentation] Pd-Catalyzed Intramolecular Amidination of Unsaturated Isothioureas : A Concise Synthesis of Indolo[2,3-b]quinolines2009

    • Author(s)
      Hiroshi Takeda, Yoshizumi Yasui, Yoshiji Takemoto
    • Organizer
      15th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis(OMCOS-15)
    • Place of Presentation
      Glasgow, UK
    • Year and Date
      2009-07-27
    • Related Report
      2009 Annual Research Report
  • [Presentation] 光学活性分子シートの構築:水素結合形成部位を有するヘリセン環状三量体の合成と組織化2009

    • Author(s)
      安井義純
    • Organizer
      20周年記念万有仙台シンポジウム
    • Place of Presentation
      仙台
    • Year and Date
      2009-06-13
    • Related Report
      2009 Annual Research Report
  • [Presentation] オレフィンの求電子的アミド化反応による不飽和ラクタムの合成2009

    • Author(s)
      安井義純、柿木原一成、竹田寛、竹本佳司
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都
    • Year and Date
      2009-03-28
    • Related Report
      2009 Final Research Report 2008 Annual Research Report
  • [Presentation] パラジウム触媒を用いた不飽和結合のアミジン化反応の開発2009

    • Author(s)
      竹田寛、安井義純、竹本佳司
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都
    • Year and Date
      2009-03-28
    • Related Report
      2009 Final Research Report 2008 Annual Research Report
  • [Presentation] 上崎春陽、安井義純、竹本佳司2009

    • Author(s)
      パラジウム触媒によるジエンの連続的アミド化-アリル位置換反応
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都
    • Year and Date
      2009-03-28
    • Related Report
      2009 Final Research Report
  • [Presentation] Synthesis of α,α-Disubstituted Lactams through Palladium-Catalyzed Enantioselective Intramolecular Amidations.2008

    • Author(s)
      Y. Yasui, H. Kamisaki, H. Takeda, Y. Takemoto
    • Organizer
      UK/Japan Joint Symposium on Asymmetric Catalysis
    • Place of Presentation
      Kyoto
    • Year and Date
      2008-12-08
    • Related Report
      2009 Final Research Report
  • [Presentation] パラジウム触媒を用いたオレフィンの分子内シアノアミド化反応によるα, α-二置換ラクタムの合成2008

    • Author(s)
      安井義純、上崎春陽、竹本佳司
    • Organizer
      第93回有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2008-06-13
    • Related Report
      2009 Final Research Report
  • [Presentation] パラジウム触媒を用いたオレフィンの分子内シアノアミド化反応によるα, α-二置換ラクタムの合成2008

    • Author(s)
      安井義純、上崎春陽、竹本佳司
    • Organizer
      第97回有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2008-06-13
    • Related Report
      2008 Annual Research Report
  • [Presentation] パラジウム触媒によるオレフィンの分子内シアノアミド化反応2008

    • Author(s)
      安井義純、上崎春陽、竹田寛、竹本佳司
    • 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
    • Related Report
      2009 Final Research Report
  • [Presentation] パラジウム触媒によるオレフィンの分子内シアノアミド化反応2008

    • Author(s)
      安井義純、上崎春陽、竹本佳司
    • Organizer
      第6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
    • Related Report
      2008 Annual Research Report
  • [Presentation] パラジウム触媒によるジエンの連続的アミド化-アリル位置換反応2008

    • Author(s)
      上崎春陽、安井義純、竹本佳司
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都
    • Year and Date
      2008-03-28
    • Related Report
      2008 Annual Research Report

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Published: 2008-04-01   Modified: 2016-04-21  

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