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2005 Fiscal Year Final Research Report Summary

Synthesis of Jellyfish-Type Macrocyclic Molecular Flask and Efficient Reaction Using the Molecular Flask

Research Project

Project/Area Number 15550039
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionKumamoto University

Principal Investigator

NISHINO Hiroshi  Kumamoto University, Science, Professor, 理学部, 教授 (50145281)

Project Period (FY) 2003 – 2005
KeywordsMolecular Flask / Cage-Type macrocyclic Copounds / Intermolecular Radical Cyclization / Intramolecular Radical Cyclization / Manganese(III) Acetate / Oxidative Radical Reaction / Cyclophene-Type Macrodiolides / 1,3-Dicarbonyl Compounds
Research Abstract

This research project was proposed that an artificial molecular flask such as a cage-type mocrocyclic compound would be synthesized and a highly efficient reaction would be carried out using the molecular flask similar to that using a protein pocket in vivo. The protein pocket in vivo is a three-dimensional hole and it is an efficient reaction flask using hydrogen bond, π-electron interaction, steric repulsion, and so on. Then we planed to synthesize an original cage-type molecular macrocyclic compound using the manganese(III)-based oxidative radical macrocyclization reaction.
We developed the manganese(III)-based oxidative radical macrocyclization reaction and the synthesis of up to dihydrofuran-fused fifty-membered macrocyclic compounds was achieved, This reaction is very efficient and the yield is also high. Therefore, we examined to synthesize the original cage-type molecular macrocyclic compounds using the manganese(III)-based oxidative radical macrocyclization reaction. When the c … More age-type macrocyclic compounds would be synthesized, it would be examined the following items ;
1) the inclusion of a guest organic compound into the cavity of the cage-type macrocyclic compounds,
2) the immobilization of the guest organic compound and reagents in the cavity using the hydrogen bond, π-electron interaction, and/or steric repulsion,
3) the highly efficient reaction of the guest organic compound with reagents in the cavity,
4) the extraction and separation of the products after the reaction,
5) the recovery and reuse of the cage-type macrocyclic compounds.
Although the cage-type macrocyclic compounds were not synthesized, sixty-five-membered cyclophene-type macrocyclic compounds were prepared. In addition, the synthesis of nine- to eighteen-membered microdiolides were achieved. Furthermore, many new guest organic molecules were synthesized.
In the near future, we will plane to investigate the functional ability of the synthesized cyclophene-type macrocyclic compounds. In the event, we will achieve the synthesis of cage-type molecular macrocyclic compounds and investigate the functional ability for the biomimetic molecular flask. Finally, we will develop the highly stereoselective organic reactions using the cage-type molecular macrocyclic compounds. Less

  • Research Products

    (13 results)

All 2006 2005

All Journal Article (12 results) Book (1 results)

  • [Journal Article] A Facile Synthesis of N,N'-Oligomethylenebis(4,5-dihydrofuran-3-carboxamide)s Using Manganese(III)-Based Radical Cyclization of N,N'-Oligomethylenebis(3-oxobutanamide)s with 1,1-Diarylethenes2005

    • Author(s)
      Firoz Alam Chowdhury, Hiroshi Nishino
    • Journal Title

      J.Heterocycl.Chem. 42

      Pages: 1337-1344

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Synthesis of 8-aza-2,3-dioxabicyclo[4.4.0]decan-7-ones using manganese(III)-catalyzed aerobic oxidation2005

    • Author(s)
      Kentaro Asahi, Hiroshi Nishino
    • Journal Title

      Heterocycl.Commun. 11

      Pages: 379-384

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] One-Pot Synthesis of Spirofuran and Benzocycloalka[1,2-b]furan Derivatives Using Mn(III)-Mediated Oxidative Radical Cyclization2005

    • Author(s)
      Reika Fujino, Hiroshi Nishino
    • Journal Title

      Synthesis 2005

      Pages: 731-740

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Photo-Induced Aromatic Assembly of Spiro[furan-2(3H),1'-benzocycloalkane] and Benzocycloalka[1,2-b]furan Derivatives2005

    • Author(s)
      Reika Fujino, Shougo Kajikawa, Hiroshi Nishino
    • Journal Title

      Tetrahedron Lett. 46

      Pages: 7303-7306

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Manganese(III)-based oxidation of 2,4-piperidinediones in the presence of alkenes2005

    • Author(s)
      Kentaro Asahi, Hiroshi Nishino
    • Journal Title

      Tetrahedron 61

      Pages: 11107-11124

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Manganese(III)-Catalyzed Facile Oxygenation of Some Cyclic 1,3-Dicarbonyl Compounds2005

    • Author(s)
      Md.Taifur Rahman, Hiroshi Nishino
    • Journal Title

      Cryogenics Report of Kumamoto University 16

      Pages: 56-61

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] A Facile Synthesis of N,N'-Oligomethylenebis(4,5-dihydrofuran-3-carboxamide)s Using Manganese(III)-Based Radical Cyclization of N,N'-Oligomethylene-bis(3-oxobutanamide)s with 1,1-Diarylethenes2005

    • Author(s)
      Firoz Alam Chowdhury, Hiroshi Nishino^*
    • Journal Title

      J.Heterocycl.Chem. 42

      Pages: 1337-1344

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Synthesis of 8-aza-2,3-dioxabicyclo[4.4.0]decan-7-ones using manganese(III)-catalyzed aerobic oxidation2005

    • Author(s)
      Kentaro Asahi, Hiroshi Nishino^*
    • Journal Title

      Heterocycl.Commun. 11(5)

      Pages: 379-384

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] One-Pot Synthesis of Spirofuran and Benzocycloalka[1,2-b]furan Derivatives Using Mn(III)-Mediated Oxidative Radical Cyclization2005

    • Author(s)
      Reika Fujino, Hiroshi Nishino^*
    • Journal Title

      Synthesis (5)

      Pages: 731-740

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Photo-Induced Aromatic Assembly of Spiro [furan-2(3H),1'-benzocycloalkane] and Benzocycloalka[1,2-b]furan Derivatives2005

    • Author(s)
      Reika Fujino, Shougo Kajikawa, Hiroshi Nishino^*
    • Journal Title

      Tetrahedron Lett. 46

      Pages: 7303-7306

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Manganese(III)-based oxidation of 2,4-piperidinediones in the presence of alkenes2005

    • Author(s)
      Kentaro Asahi, Hiroshi Nishino^*
    • Journal Title

      Tetrahedron 61/47

      Pages: 11107-11124

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Manganese(III)-Catalyzed Facile Oxygenation of Some Cyclic 1,3-Dicarbonyl Compounds2005

    • Author(s)
      Md.Taifur Rahman, Hiroshi Nishino^*
    • Journal Title

      Cryogenics Report of Kumamoto University 16

      Pages: 56-61

    • Description
      「研究成果報告書概要(欧文)」より
  • [Book] Manganese(III)-Based Peroxidation of Alkenes to Heterocycles2006

    • Author(s)
      Hiroshi Nishino
    • Publisher
      Springer(印刷中)
    • Description
      「研究成果報告書概要(和文)」より

URL: 

Published: 2007-12-13  

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