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2005 Fiscal Year Final Research Report Summary

Investigation of new biologically active compounds containing a dendrimer skeleton

Research Project

Project/Area Number 15550036
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionOKAYAMA UNIVERSITY

Principal Investigator

TSUBOI Sadao  OKAYAMA UNIVERSITY, Graduate School of Environment, Professor, 大学院環境学研究科, 教授 (00032954)

Co-Investigator(Kenkyū-buntansha) TAKAGUCHI Yutaka  OKAYAMA UNIVERSITY, Graduate School of Environment, Associate Professor, 大学院環境学研究科, 助教授 (10293482)
Project Period (FY) 2003 – 2005
Keywordsfullarodendrimer / Darzen's condensation / Pyrones / butenolide / verrcosapyrone A / 3-DPA lactone / anticancer activity / antibiotics
Research Abstract

This project consists of investigation of the synthesis of biologically active compounds, which can be utilized for new medicines. These materials have dendrimer skeletone and biologically active components. Research interest of head investigator was the synthesis of biologically active compounds for a long time. Another investigator has developed new chemistry of fullarodendrimers. Head investigator synthesized many oxygen-contaning biologically active compounds such as anticancer and antibiotics by Darzen's condensation (reaction of aldehydes and dichloroacetates in the presence of base) as a key step. In this research, head investigator discovered a new synthetic method of alpha-hydroxy butenolides by the treatment of glycidic esters with MgCl_2, and 3-DPA lactone was prepared. Head investigator found out treatment of alpha-chloroglycidic esters (1) with triphenylphosphine gives 3-chloro-2-ketoesters (2). Furthermore, treatment of 1 with potassium acetate gave 2-acetoxy-3-ketoesters (3) newly. By this new reaction, (-)-verrucosapyrone A (4) was synthesized and the absolute configuration of its one carbon was clarified. The structure of 4 is similar to that of pestalotin, of which has an activity of promotor of plant growth. So, many biological activities would be expected. New pyrone synthesis from acetonide-protected glycidate (1) was also reported.
In a future, connection of newly prepared oxygen-containing cyclic compounds with fullarodendrimer will be established, and biological activities of these final products would be investigated.
In this project, many new results were obtained and thirteen papers were published in valuable journals.

  • Research Products

    (28 results)

All 2007 2006 2005 2004

All Journal Article (28 results)

  • [Journal Article] One-pot Synthesis of 2-Arylthio-2-cyclohexenone by the Diels-Alder Reaction of 4-Arylthio-3-hydroxy-2-pyrone2007

    • Author(s)
      Komiyama, T., Takaguchi Y., Tsuboi, Sadao
    • Journal Title

      2. Synth. Commun. 2007, 37 37(in press)

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Synthesis of 4-Arylthio-3-hydroxyphthalate by the Diels-Alder Reaction of 4-Arylthio-3-hydroxy-2-pyrone2007

    • Author(s)
      Komiyama, T., Takaguchi Y., Tsuboi, Sadao
    • Journal Title

      Synth. Commun. 37

      Pages: 531

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Synthesis of 4-Arylthio-3-hydroxyphthalate by the Diels-Alder Reaction of 4-Arylthio-3-hydroxy- 2-pyrone2007

    • Author(s)
      Komiyama T., Takaguchi Y., Tsuboi Sadao
    • Journal Title

      Synthetic Commun. 37

      Pages: 531-534

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] One-pot Synthesis of 2-Arylthio-2-cyclohexenone by the Diels-Alder Reaction of 4-Arylthio-3-hydroxy- 2-pyrone2007

    • Author(s)
      Komiyama T., Takaguchi Y., Tsuboi S.
    • Journal Title

      Synth. Commun. 27(in press)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Synthesis of 4-Arylthio-3-hydroxyphthalate by the Diels-Alder Reaction of 4-Arylthio-3-hydroxy- 2-pyrone2007

    • Author(s)
      Komiyama T., Takaguchi Y., Tsuboi S.
    • Journal Title

      Synth. Commun. 37

      Pages: 531-534

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] One Pot Substitution-Rearrangement Reaction of 2-Chloroglycidic Ester : Effective Protocole for the Preparation of 3-Arylsulfenyl-2-keto Ester2006

    • Author(s)
      Komiyama, T., Takaguchi Y., Tsuboi, Sadao
    • Journal Title

      Synth. Commun 36

      Pages: 265

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Synthesis of Anthraquinone Derivatives : Tandem Tsuboi Diels-Alder-Decarboxylation-Oxidation Reaction of 3-Hydroxy-2-pyrone with 1,4-Naphthoquinone2006

    • Author(s)
      Komiyama, T., Takaguchi Y., Tsuboi Sadao
    • Journal Title

      Synlett 2006

      Pages: 124

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Efficient One Pot Synthesis of 5-Hydroxy-1,4-naphthoquinone2006

    • Author(s)
      Komiyama, T., Takaguchi, Y., Tsuboi, S
    • Journal Title

      Synthesi 2006

      Pages: 1405

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Novel and Effective Synthesis of 2-Acyloxy-3-keto Ester2006

    • Author(s)
      Komiyama, T., Takaguchi, Y., Tsuboi, S.
    • Journal Title

      Synthesi 2006

      Pages: 1767

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Convenient Rearrangement Reaction of 2-Chloroglycidic Ester by PPh_3 : A New Synthesis of 3-Chloro-2-keto Ester2006

    • Author(s)
      Komiyama, T., Takaguchi Y., Tsuboi, Sadao
    • Journal Title

      Synth. Commun 36

      Pages: 2621

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] First total synthesis of (±)-verrucosapyrone A2006

    • Author(s)
      Komiyama, T., Takaguchi Y., Tsuboi, Sadao
    • Journal Title

      Synthesis 2006

      Pages: 4115

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Asymmetric Synthesis of (-)-Verrucosapyrone A by the Biocatalyst and Determination of its Absolute Configuration2006

    • Author(s)
      Komiyama, T., Takaguchi Y., Tsuboi, Sadao
    • Journal Title

      Heterocycle 68

      Pages: 1451

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] 1. Novel Synthesis of 3-DPA Lactone via Tandem Cyclization Reaction of Acetonide Protected 4,5-Dihydroxy-2-chloroglycidic ester" Heterocycles 2006, 68, 1925-1930.2006

    • Author(s)
      Komiyama, T., Takaguchi Y., Tsuboi, Sadao
    • Journal Title

      Heterocycle 68

      Pages: 1925

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Asymmetric Synthesis of (-)-verrucosapyrone A by Biocatalyst and Determination of its Absolute Configuration2006

    • Author(s)
      Komiyama T., Takaguchi Y., Tsuboi Sadao
    • Journal Title

      Heterocycles 68

      Pages: 1451-1454

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Synthesis of 3-DPA Lactone via Tandem Cyclization Reaction of Acetonide Protected Methyl 4,5-Dihydroxy-2-chloroglycidate2006

    • Author(s)
      Komiyama T., Takaguchi Y., Tsuboi Sadao
    • Journal Title

      Heterocycles 68

      Pages: 1925-1930

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] One Pot Substitution-Rearrangement Reaction of 2- Chloroglycidic Ester : Effective Protocole for the Preparation of 3-Arylsulfenyl-2-keto Ester2006

    • Author(s)
      Komiyama T., Takaguchi Y., Tsuboi Sadao
    • Journal Title

      Synth. Commun 36

      Pages: 265

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Synthesis of Anthraquinone Derivatives : Tandem Diels-Alder-Decarboxylation-Oxidation Reaction of 3-Hydroxy-2-pyrone with 1,4-Naphthoquinone2006

    • Author(s)
      Komiyama T., Takaguchi Y., Tsuboi Sadao
    • Journal Title

      Synlett

      Pages: 124-126

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Efficient One Pot Synthesis of 5-Hydroxy- 1,4-naphthoquinone2006

    • Author(s)
      Komiyama T., Takaguchi Y., Tsuboi Sadao.
    • Journal Title

      Synthesis

      Pages: 1405-1407

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Novel and Effective Synthesis of 2-Acyloxy-3-keto Esters2006

    • Author(s)
      Komiyama T., Takaguchi Y., Tsuboi Sadao
    • Journal Title

      Synthesis

      Pages: 1767-1770

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] First total Synthesis of (±)-Verrucosapyrone A2006

    • Author(s)
      Komiyama T., Takaguchi Y., Tsuboi Sadao
    • Journal Title

      Synthesis

      Pages: 4115-4117

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Novel Synthesis of 4-Halo-3-hydroxy-2-pyrone : One Pot Rearrange- ment-Cyclization Reaction by Magnesium Halide2005

    • Author(s)
      Komiyama, T., Takaguchi, Y., Gubaidullin, A.T., Mamedov, V.A., Litvinov, I.A., Tsuboi, S.
    • Journal Title

      Tetrahedron 61

      Pages: 2541

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Novel plotocol for the Asymmetric Synthesis of 3-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1, 5-benzothiaze pin- 4(5H)-one via Bakers' Yeast Reduction2005

    • Author(s)
      Komiyama, T., Takaguchi Y., Tsuboi Sadao
    • Journal Title

      Heterocycles 66

      Pages: 147

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Novel Synthesis of 4-Arylsulfenyl-3-hydroxy-2-pyrone : One pot Substitution-Rearrangement- Cyclization Reaction of Acetonide Protected 4,5-Dihydroxy-2-chloroglycidic Esters by Sodium Arylthiolate2005

    • Author(s)
      Komiyama, T., Takaguchi Y., Tsuboi, Sadao
    • Journal Title

      Heterocycles 66

      Pages: 503

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Novel Synthesis of 4-Halo-3-hydroxy-2-pyrone : One Pot Rearrange-ment-Cyclization Reaction by Magnesium Halide2005

    • Author(s)
      Komiyama T., Takaguchi Y., Gubaidullin A.T., Mamedov V.A., Litvinov I.A., Tsuboi S.
    • Journal Title

      Tetrahedron 61

      Pages: 6541-2547

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Novel plotocol for the Asymmetric Synthesis of 3-Hydroxy-2-(4-methoxypheny1)-2,3-dihydro-1,5- benzothiazepin-4(5H)-one via Bakers' Yeast Reduction2005

    • Author(s)
      Komiyama T., Takaguchi Y., Tsuboi Sadao
    • Journal Title

      Heterocycles 66

      Pages: 147-151

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Novel Synthesis of 4-arylsulfeny1-3-hydroxy-2- pyrone : One Pot Substitution-Rearrangement- Cyclization Reaction of Acetonide Protected 4,5- Dihydroxy-2-chloroglycidic Ester by Sodium Arylthiolate2005

    • Author(s)
      Komiyama T., Takaguchi Y., Tsuboi Sadao
    • Journal Title

      Heterocycles 66

      Pages: 503-509

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Novel Synthesis of 4-Chloro-3-hydroxy-2-pyrone by the Reaction of Acetonide Protected 4,5-Dihydroxy-2- chloroglycidic Ester with Magnesium Chloride2004

    • Author(s)
      Komiyama, T., Takaguchi, Y., Tsuboi, S
    • Journal Title

      Tetrahedron Lett 45

      Pages: 6299

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Novel Synthesis of 4-Chloro-3-hydroxy-2-pyrone by the Reaction of Acetonide Protected 4,5-Dihydroxy-2- chloroglycidic Ester with Magnesium Chloride2004

    • Author(s)
      Komiyama T., Takaguchi Y., Tsuboi S.
    • Journal Title

      Tetrahedron Lett 46

      Pages: 6299-6301

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 2008-05-27  

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