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Efficient Preparation of Biaryl Compounds and Its Application

Research Project

Project/Area Number 18590005
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionOkayama University

Principal Investigator

ABE Hitoshi  Okayama University, Advanced Science Research Center, Associate Professor (70221728)

Project Period (FY) 2006 – 2007
Project Status Completed (Fiscal Year 2007)
Budget Amount *help
¥3,950,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2007: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2006: ¥2,000,000 (Direct Cost: ¥2,000,000)
KeywordsPalladium Reagent / Biaryl Compound / Natural Pruduct Synthesis / Regioselectivity / エラジタンニン / フェニルベンゾエート / パラジウム / 保護基 / ベンゾナフトアミド / 動的速度論的光学分割 / 軸不斉
Research Abstract

Biaryl compounds are important building blocks for naturally occurring materials, and the methods for forming carbon-carbon bond between two aromatic rings have been developed for over 100 years. As a classical method, the Ullmann coupling has been a standard transformation to prepare biaryl molecules although this method often requires the vigorous reaction conditions. Additionally, in the Ullmann coupling, there are some difficulties for the synthesis of unsymmetrical biaryl molecules.
For more convenient procedure, Suzuki-Miyaura coupling reaction has widely been utilized for the biaryl synthesis, as well as Stille coupling reaction. For these transformations, the functionalization on both of aromatic rings are necessary, i.e. halogenation on one aromatic ring, and the introduction of boron or tin atom on the other one. However, two aromatic rings, if they are linked with ester or amide group each other, can be coupled using Pd reagent without introduction of the functional group on one aromatic ring. Under such a concept, the intramolecular Pd-mediated biaryl coupling reactions have been developed to synthesize many polycyclic aromatic compounds including some natural products.

Report

(3 results)
  • 2007 Annual Research Report   Final Research Report Summary
  • 2006 Annual Research Report
  • Research Products

    (40 results)

All 2008 2007 2006 Other

All Journal Article (14 results) (of which Peer Reviewed: 6 results) Presentation (26 results)

  • [Journal Article] Enantioselective Synthesis of Valoneic Acid Derivative2008

    • Author(s)
      Hitoshi Abe
    • Journal Title

      Tetrahedron Letters 49

      Pages: 605-609

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Annual Research Report 2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Palladium-Mediated Intramolecular Biaryl Coupling Reaction for Natural Product Synthesis2008

    • Author(s)
      Hitoshi Abe
    • Journal Title

      Heterocycles 75(印刷中)

    • NAID

      40016054546

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Annual Research Report 2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Synthesis of Highly Oxygenated Biphenyl Derivative in an Optically Active Form through Palladium-Mediated Intramolecular Biaryl Coupling Reaction2008

    • Author(s)
      Hitoshi Abe
    • Journal Title

      Heterocycles 76(印刷中)

    • NAID

      40016208574

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Annual Research Report 2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Enantioselective Synthesis of Valoneic Acid Derivative2008

    • Author(s)
      Abe, H., Sahara, Y., Matsuzaki, Y., Takeuchi, Y., Harayama, T
    • Journal Title

      Tetrahedron Lett 49

      Pages: 605-609

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Intramolecular Biaryl Coupling Reaction of Benzyl Benzoate and Phenyl Benzoate Derivatives, and Its Application to the Formal Synthesis of (-)-Steganone2007

    • Author(s)
      Shigemitsu Takeda
    • Journal Title

      Tetrahedron 63

      Pages: 396-408

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Synthesis of Alternariol through an Intramolecular Biaryl Coupling Reaction Using Palladium Reagent2007

    • Author(s)
      Hitoshi Abe
    • Journal Title

      Heterocycles 74

      Pages: 265-271

    • NAID

      40015919587

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Annual Research Report 2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Intramolecular Biaryl Coupling Reaction of Benzyl Benzoate and Phenyl Benzoate Derivatives, and Its Application to the Formal Synthesis of (-)-Steganone2007

    • Author(s)
      Takeda, S., Abe, H., Takeuchi, Y., Harayama, T
    • Journal Title

      Tetrahedron 63

      Pages: 396-408

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Synthesis of Alternariol through an Intramolecular Biaryl Coupling Reaction Using Palladium Reagent2007

    • Author(s)
      Abe, H., Fukumoto, T., Takeuchi, Y., Harayama, T
    • Journal Title

      Heterocycles 74

      Pages: 265-271

    • NAID

      40015919587

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Intramolecular Biaryl Coupling Reaction of Benzyl Benzoate and Phenyl Benzoate Derivatives, and Its Application to the Formal Synthesis of (-)-Steganone2007

    • Author(s)
      Shigemitsu Takeda
    • Journal Title

      Tetrahedron 63巻・2号

      Pages: 396-408

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Syntheses of Ulocladol2006

    • Author(s)
      Hitoshi Abe
    • Journal Title

      Heterocycles 69

      Pages: 217-222

    • NAID

      40015163896

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Syntheses of Ulocladol2006

    • Author(s)
      Abe, H., Fukumoto, T., Nishioka, K., Arai, M., Takeuchi, Y., Harayama, T
    • Journal Title

      Heterocycles 69

      Pages: 217-222

    • NAID

      40015163896

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Syntheses of Ulocladol2006

    • Author(s)
      Hitoshi Abe
    • Journal Title

      Heterocycles 69巻・1号

      Pages: 217-222

    • NAID

      40015163896

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Palladium-Mediated Intramolecular Biaryl Coupling Reaction for Natural Product Synthesis

    • Author(s)
      Abe, H., Harayama, T
    • Journal Title

      Heterocycles (in press)

    • NAID

      40016054546

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Synthesis of Highly Oxygenated Biphenyl Derivative in an Optically Active Form through Palladium-Mediated Intramolecular Biaryl Coupling Reaction

    • Author(s)
      Abe, H., Arai, M., Nishioka, K., Kida, T., Shioe, K., Takeuchi, Y., Harayama, T
    • Journal Title

      Heterocycles (in press)

    • NAID

      40016208574

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Valoneic acid誘導体の不斉合成2008

    • Author(s)
      阿部仁
    • Organizer
      日本薬学会第128年会
    • Place of Presentation
      横浜
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Annual Research Report 2007 Final Research Report Summary
  • [Presentation] Alternariol及びgraphislactone Gの合成2007

    • Author(s)
      福本倫子
    • Organizer
      日本薬学会第127年会
    • Place of Presentation
      富山
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Zanthoxyline及び関連塩基の合成研究2007

    • Author(s)
      小林尚子
    • Organizer
      日本薬学会第127年会
    • Place of Presentation
      富山
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Synthesis of Zanthoxyline and Related Compounds2007

    • Author(s)
      Hitoshi Abe
    • Organizer
      International Congress for Heterocyclic Chemistry(ICHC-21)
    • Place of Presentation
      Sydney
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Palladium-and/or Copper-Mediated Intramolecular Cyclizations Applied for the Synthesis of Benzo[h]quinoline Skeleton2007

    • Author(s)
      Georgeta Serban
    • Organizer
      14th IUPAC International Symposium on Organometallic Chemistry Directed towards Organic Synthesis(OMCOS-14)
    • Place of Presentation
      Nara
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Zanthoxylineの合成と構造訂正2007

    • Author(s)
      阿部仁
    • Organizer
      第33回反応と合成の進歩シンポジウム
    • Place of Presentation
      長崎
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Annual Research Report 2007 Final Research Report Summary
  • [Presentation] Pd触媒系を用いたフェニルベンゾエート誘導体の閉環反応:位置選択性に関する検討2007

    • Author(s)
      前田和洋
    • Organizer
      第46回日本薬学会・日本病院薬剤師会中国四国支部学術大会
    • Place of Presentation
      高知
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Annual Research Report 2007 Final Research Report Summary
  • [Presentation] Synthesis of Alternariol and Graphislactone G2007

    • Author(s)
      Tomoko, Fukumoto, et. al.
    • Organizer
      127th Annual Meeting of Pharmaceutical Society of Japan
    • Place of Presentation
      Toyama
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Synthesis of Zanthoxyline and Related Alkaloids2007

    • Author(s)
      Naoko, Kobayashi, et. al.
    • Organizer
      127th Annual Meeting of Pharmaceutical Society of Japan
    • Place of Presentation
      Toyama
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Synthesis of Zanthoxyline and Relatec Compounds2007

    • Author(s)
      Hitoshi, Abe, et. al.
    • Organizer
      International Congress for Heterocyclic Chemistry (ICHC-21)
    • Place of Presentation
      Sydney
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Palladium-and/or Copper-Mediated Intramolecular Cyclizations Applied for the Synthesis of Benzo[h] quinoline Skeleton2007

    • Author(s)
      Georgeta, Serban, et. al.
    • Organizer
      14th IUPAC International Symposium on Organometallic Chemistry Directed towards Organic Synthesis (OMCOS-14)
    • Place of Presentation
      Nara
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Synthesis of Zanthoxyline an Revision of the Proposed Structure2007

    • Author(s)
      Hitoshi, Abe, et. al.
    • Organizer
      33rd Symposium on Progress in Organic Reactions and Syntheses
    • Place of Presentation
      Nagasaki
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Cyclization of Phenyl benzoate derivatives Using Palladium Catalyst : Investigation of the Regioselectivity2007

    • Author(s)
      Kazuhiro, maeda, et. al.
    • Organizer
      The 46th Annual Meeting of Chugoku branch of Pharmaceutical Society
    • Place of Presentation
      Japan (Kochi)
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Asymmetric Synthesis of Valoneic Acid Derivative2007

    • Author(s)
      Hitoshi, Abe, et. al.
    • Organizer
      128th Annual Meeting of Pharmaceutical Society of Japan
    • Place of Presentation
      Yokohama
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Synthesis of Zanthoxyline and Related Compounds2007

    • Author(s)
      Hitoshi Abe
    • Organizer
      International Congress for Heterocyclic Chemistry (ICHC-21)
    • Place of Presentation
      Sydney
    • Related Report
      2007 Annual Research Report
  • [Presentation] Palladium- and/or Copper-Mediated Intramolecular Cyclizations Applied for the Synthesis of Benzo[h] quinoline Skeleton2007

    • Author(s)
      Georgeta Serban
    • Organizer
      14th IUPAC International Symposium on Organometallic Chemistry Directed towards Organic Synthesis (OMCOS-14)
    • Place of Presentation
      Nara
    • Related Report
      2007 Annual Research Report
  • [Presentation] Synthesis of Ulocladol by an Intramolecular Aryl-Aryl Coupling Reaction2006

    • Author(s)
      Hitoshi Abe
    • Organizer
      International Conference on Biodiversity and Natural Products (ICOB-5 & ISCNP-25)
    • Place of Presentation
      Kyoto
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Valoneic acid誘導体の合成研究2006

    • Author(s)
      佐原有亮
    • Organizer
      第45回日本薬学会・日本病院薬剤師会中国四国支部学術大会
    • Place of Presentation
      広島
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Zanthoxyline及び関連塩基の合成研究2006

    • Author(s)
      小林尚子
    • Organizer
      第45回日本薬学会・日本病院薬剤師会中国四国支部学術大会
    • Place of Presentation
      広島
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Asymmetric Synthesis of Highly Oxygenated Biphenyl Compounds by an Intramolecular Aryl-Aryl Coupling Reaction2006

    • Author(s)
      Hitoshi Abe
    • Organizer
      The 10th International Kyoto Conference on New Aspects of Organic Chemistry(IKCOC-10)
    • Place of Presentation
      Kyoto
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] パラジウム触媒を用いた分子内カップリングを経由するビフェニル化合物の合成2006

    • Author(s)
      佐原有亮
    • Organizer
      第32回反応と合成の進歩シンポジウム
    • Place of Presentation
      広島
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Synthesis of Ulocladol by an Intramolecular Aryl-Aryl Coupling Reaction2006

    • Author(s)
      Hitoshi, Abe, et. al.
    • Organizer
      International Conference on Biodiversity and Natural Products (ICOB-5 & ISCNR-25)
    • Place of Presentation
      Kyoto
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Synthetic Study of Valoneic Acid2006

    • Author(s)
      Yusuke, Sahara, et. al.
    • Organizer
      The 45th annual meeting of Chugoku-Shikoku branch of Pharmaceutical Society
    • Place of Presentation
      Japan (Hiroshima)
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Synthetic Study of Zanthoxyline and Related Alkaloids2006

    • Author(s)
      Naoko, Kobayashi, et. al.
    • Organizer
      The 45th Annual Meeting of Chugoku-Shikoku branch of Pharmaceutical Society
    • Place of Presentation
      Japan (Hiroshima)
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Asymmetric Synthesis of Highly Oxygenated Biphenyl Compounds by an Intramolecular Aryl-Aryl Coupling Reaction2006

    • Author(s)
      Hitoshi, Abe, et. al.
    • Organizer
      The 10th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-10)
    • Place of Presentation
      Kyoto
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Synthesis of Biphenyl Compounds through Intramolecular Coupling Reaction Using Palladium Catalyst2006

    • Author(s)
      Yusuke, Sahara, et. al.
    • Organizer
      32rd Symposium on Progress in Organic Reactions and Syntheses
    • Place of Presentation
      Hiroshima
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary

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Published: 2006-04-01   Modified: 2016-04-21  

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