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Novel synthesis of indole derivatives based on the palladium catalyzed cross-coupling reaction with indolylborates as a key reaction

Research Project

Project/Area Number 09672151
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionHealth Sciences University of Hokkaido

Principal Investigator

ISHIKURA Minoru  Health Sciences University of Hokkaido, Faculty of Pharmaceutical Sciences, associate Prof., 薬学部, 助教授 (10146011)

Co-Investigator(Kenkyū-buntansha) KATAGIRI Nobuya  Health Sciences University of Hokkaido, Faculty of Pharmaceutical Sciences, Prof., 薬学部, 教授 (60089787)
縣 功  北海道医療大学, 薬学部, 教授 (40094825)
Project Period (FY) 1997 – 1999
Project Status Completed (Fiscal Year 1999)
Budget Amount *help
¥3,100,000 (Direct Cost: ¥3,100,000)
Fiscal Year 1999: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1998: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1997: ¥1,900,000 (Direct Cost: ¥1,900,000)
Keywordsindolylborate / indole / borate / cross-coupling reaction / ellipticine / yuehchukene / 生物活性物質 / パラジウム触媒 / エリプチシン / yuehchukene / 一酸化炭素 / インドール誘導体 / アレニルインドール
Research Abstract

Indolylborates, readily available from the corresponding 2-lithioindoles and triethylborane in situ, are valuable synthetic intermediates, and the development of their synthetic capabilities has been our continuing interest. During these studies, the palladium catalyzed cross-coupling reaction with indolylborates has been proven to be an effective protocol for the preparation of substituted indole derivatives. In these studies, the followings have been achieved by the use of the cross-coupling reaction as a key reaction;
1. Synthesis of ellipticine and its analogues by the palladium catalyzed tandem cyclization cross-coupling reaction
2. Synthesis of yuehchukene and its analogues by the palladium catalyzed carbonylative cross-coupling reaction.

Report

(4 results)
  • 1999 Annual Research Report   Final Research Report Summary
  • 1998 Annual Research Report
  • 1997 Annual Research Report
  • Research Products

    (22 results)

All Other

All Publications (22 results)

  • [Publications] Minoru Ishikura: "Investigation of the Reaction of N-Substituted Indolylborates: Palladium Catalyzed Cross-Coupling Reactions and Intramolecular Alkyl Migration Reactions"J.Heterocyclic Chem.. 36. 873-879 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Minoru Ishikura: "A Novel Entry to Pyrodo[4.3-b]carbozoles: An Efficient Synthesis of Ellipticine"Tetrahedron. 56. 193-207 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Minoru Ishikura: "An Efficient Total Synthesis of Ellipticine"Heterocycles. 53. 11-14 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Minoru Ishikura: "Total Synthesis of Yuehchukene"Heterocycles. 53. 553-556 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Minoru Ishikura: "Organicboron Compounds and Organic Synthesis - Novel synthesis of heterocyclic compounds (2)"The Chemical Times. (2). 5-11 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Minoru Ishikura and Isao Agata: "Indolylborate: A potential synthetic intermediate"Recent. Res. Devel. In Organic Chem.. 1. 145-157 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Minoru Ishikura, Yukinori Matsuzaki, and Isao Agata: Heterocycles. 45. 2309-2312 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Minoru Ishikura, Toshikatsu Yaginuma, Isao Agata, Yoshihisa Miwa, Reiko Yanada, and Tooru Taga: Synlett. 214-216 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Minoru Ishikura, Yukinori Matsuzaki, Isao Agata, and Nobuya Katagiri: "A concise access to allenylindole derivatives based on the palladium catalyzed cross-coupling reaction of indolylborates"Tetrahedron. 54. 13929-13942 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Minoru Ishikura, Lsao Agata, and Nobuya Katagiri: "Investigation of the reaction of N-substituted indolylborates: Palladium catalyzed cross-coupling reactions and intramolecular alkyl migration reactions"J. Heterocyclic Chem.. 36. 873-879 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Minoru Ishikura, Ayako Hino; and Nobuya Katagiri: "An efficient synthesis of ellipticine"Heterocycles. 53. 11-14 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Minoru Ishikura, Ayako Hino, Toshikatsu Yaginuma, Isao Agata, and Nobuya Katagiri: "A novel entry to pyrido[4,3-b]carbazoles: Asn efficient synthesis of ellipticine."Tetrahedron. 56. 193-207 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Minoru Ishikura, Toshikatsu Imaizumi, and Nobuya Katagiri: "Total synthesis of yuehjchukene"Heterocycles. 53. 553-556 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Minoru Ishikura: "Investigation of the Reaction of N-Substituted Indolylborates:Palladium Catalyzed Cross-Coupling Reactions and Intramolecular Alkyl Migration Reactions"J.Heterocyclic Chem.. 36. 873-879 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Minoru Ishikura: "A Novel Entry to Pyrido[4.3-b]carbazoles: An Efficient Synthesis of Ellipticine"Tetrahedron. 56. 193-207 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] Minoru Ishikura: "An Efficient Total Synthesis of Ellipticine"Heterocycles. 53. 11-14 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] Minoru Ishikura: "Total Synthesis of Yuehchukene"Heterocycles. 53(in press). (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] Minoru Ishikura: "A concise access to 2-allenylindole derivatives based on the palladium catalyzed cross-coupling reaction of indolylborates" Tetrahedron. 54. 13929-13942 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Minoru Ishikura: "Investigation on the reaction of N-substituted indolylborates;palladium catalyzed cross-coupling reaction and intramolecular alkyl migration" J.Heterocyclic Chem.(in press). (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] 石倉 稔: "Palladium catalysed cross-coupling reaction with indolyborate:A concise access to ellipticine derivatives." Synlett. 2. 214-216 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 石倉 稔: "The use of the N-substituted triethylcindol-2-yl)borate for the palladium catalyzed cross-coupling reaction" Heterocycles. 45(12). 2309-2312 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 石倉 稔: "Recent Research Developments in Organic Chemistry" Transworld Research Network, 24 (1998)

    • Related Report
      1997 Annual Research Report

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Published: 1997-04-01   Modified: 2016-04-21  

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