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Synthetic Studies of Anti-tumor Natural Products Based on the Carbohydrate Transformation

Research Project

Project/Area Number 15350027
Research Category

Grant-in-Aid for Scientific Research (B)

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

Principal Investigator

NORITAKA Chida  Keio University, Faculty of Science and Technology, Professor, 理工学部, 教授 (50197612)

Project Period (FY) 2003 – 2006
Project Status Completed (Fiscal Year 2006)
Budget Amount *help
¥11,400,000 (Direct Cost: ¥11,400,000)
Fiscal Year 2006: ¥2,800,000 (Direct Cost: ¥2,800,000)
Fiscal Year 2005: ¥2,800,000 (Direct Cost: ¥2,800,000)
Fiscal Year 2004: ¥2,800,000 (Direct Cost: ¥2,800,000)
Fiscal Year 2003: ¥3,000,000 (Direct Cost: ¥3,000,000)
KeywordsCarbohydrate Transformation / Anti-tumor Natural Product / Taxol / Actinobolin / Fumagillol / Ferrier's Carbocyclization / Three-component Coupling Reaction / Total Synthesis / 抗腫瘍性天然有機化合物 / ビッタチン / D-グルコース
Research Abstract

The development of efficient chemical process for the synthesis of biologically active natural product is highly important task in modern synthetic organic chemistry. In this study, synthesis of natural products possessing significant anti-tumor activities, such as taxol, actinobolin and fumagillol based on the carbohydrate transformation was investigated. Carbohydrates have been produced by plants in huge quantities without causing any negative effect to the environment of the earth and thus are considered to be important carbon resources.
In the project of taxol synthesis, D-glucal which is one of the most readily available carbohydrates, was converted into the highly functionalized cyclohexenone derivative utilizing Ferrier's carbocyclization reaction as the key step. Three-component coupling reaction of the cyclohexenone with vinyl metal species and formaldehyde effectively afforded the C-ring of taxol.
Coupling reaction of the C-ring with A-ring, followed by further manipulation gav … More e the cyclohexenone derivative possessing an aldehyde function. SmI2 mediated reductive cyclization successfully afforded the taxane skeleton in good yield. Introduction of the carbon-carbon double bond, which would complete the total synthesis, is now under investigation.
In the synthetic study of actinobolin, total synthesis of both enantiomers of the target compound was successfully achieved.
Three-component coupling reaction of the cyclohexenone derived from D-glucose with vinyl metal species and hydroxyaldehyde was employed as the key transformation. It was found that the stereochemical control of the aldol reaction process was possible by the choice of the protecting group of the hydroxyaldehyde and the solvents.
In fumagillol synthesis, Claisen rearrangement of the cyclohexenol derived from D-glucose effectively generated the carbon-carbon bond stereoselectively. Further transformation of the rearranged product provided the Sorensen's intermediate for fumagillol, completing the formal total synthesis. Optimization of the reaction conditions is currently under way. Less

Report

(5 results)
  • 2006 Annual Research Report   Final Research Report Summary
  • 2005 Annual Research Report
  • 2004 Annual Research Report
  • 2003 Annual Research Report
  • Research Products

    (22 results)

All 2006 2005 2004 2003 Other

All Journal Article (21 results) Publications (1 results)

  • [Journal Article] Total Synthesis of Actinobolin from D-Glucose by Way of the Stereoselective Three-component Coupling Reaction2006

    • Author(s)
      Satoshi Imuta
    • Journal Title

      Tetrahedron 62・29

      Pages: 6926-6944

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] One-step Construction of Carbazoles by Way of the Palladium-catalyzed Double N-Arylation Reaction and Its Application to the Total Synthesis of Murrastifoline-A2006

    • Author(s)
      Takafumi Kitawaki
    • Journal Title

      Tetrahedron 62・29

      Pages: 6792-6801

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Total Synthesis of Dapiramicin B2006

    • Author(s)
      Hiroyuki Ohno
    • Journal Title

      Tetrahedron Letters 47・32

      Pages: 5747-5750

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Annual Research Report 2006 Final Research Report Summary
  • [Journal Article] Total Synthesis of Actinobolin from D-Glucose by Way of the Stereoselective Three-component Coupling Reaction2006

    • Author(s)
      Satoshi Imuta
    • Journal Title

      Tetrahedron 62

      Pages: 6926-6944

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] One-step Construction of Carbazoles by Way of the Palladium-catalyzed Double N-Arylation Reaction and Its Application to the Total Synthesis of Murrastifoline-A2006

    • Author(s)
      Takafumi Kitawaki
    • Journal Title

      Tetrahedron 62

      Pages: 6791-6801

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Total Synthesis of Dapiramicin B2006

    • Author(s)
      Hiroyuki Ohno
    • Journal Title

      Tetrahedron Letters 47

      Pages: 5747-5750

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Total Synthesis of Stevastelins : Structure Confirmation of Stevastelin B and B3, and Structure Revision of Stevastelin C32006

    • Author(s)
      Kazuo Kurosawa
    • Journal Title

      Bulletin of the Chemical Society of Japan 79・6

      Pages: 921-937

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Total Synthesis of Actinobolin from D-Glucose by Way of the Stereoselective Three-component Coupling Reaction2006

    • Author(s)
      Satoshi Imuta
    • Journal Title

      Tetrahedron 62・27

      Pages: 6926-6944

    • Related Report
      2006 Annual Research Report
  • [Journal Article] One-step Construction of Carbazoles by Way of the Palladium-catalyzed Double N-Arylation Reaction and Its Application to the Total Synthesis of Murrastifoline-A2006

    • Author(s)
      Takafumi Kitawaki
    • Journal Title

      Tetrahedron 62・27

      Pages: 6792-6801

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Total Synthesis and Biological Activities of (+)-Sulfamisterin (AB5366) and Its Analogues2005

    • Author(s)
      Hideyuki Sato
    • Journal Title

      The Journal of Antibiobics 58・1

      Pages: 37-49

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Total Synthesis of Murrastifoline-A by Way of The Pd-Catalyzed Double N-Arylation of A Carbazolamine with A 2,2'-Diboromobiphenyl Derivative2005

    • Author(s)
      Takafumi Kitawaki
    • Journal Title

      Heterocycles 65・7

      Pages: 1561-1567

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Total Synthesis of Stevastelins B3 and C3 : Structure Confirmation of Stevastelin B3 and Revision of Stevastelin C32005

    • Author(s)
      Kazuo Kurosawa
    • Journal Title

      Tetrahedron Letters 46・3

      Pages: 389-392

    • Related Report
      2004 Annual Research Report
  • [Journal Article] A New Entry to Amaryllidaceae Alkaloids from Carbohydrates : Total Synthesis of (+)-Vittatine2004

    • Author(s)
      Masahiro Bohno
    • Journal Title

      Chemical Communications 2004・9

      Pages: 1086-1087

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] A New Entry to Amaryllidaceae Alkaloids from Carbohydrates : Total Synthesis of (+)-Vittatine2004

    • Author(s)
      Masahiro Bohno
    • Journal Title

      Chemical Communications 2004

      Pages: 1086-1087

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] A New Entry to Amaryllidaceae Alkaloids from Carbohydrates : Total Synthesis of (+)-Vittatine2004

    • Author(s)
      Masahiro Bohno
    • Journal Title

      Chemical Communications 9

      Pages: 1086-1087

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Overman転位反応を鍵反応とした糖質からのα-置換α-アミノ酸構造を有する天然物の全合成2004

    • Author(s)
      佐藤 英之
    • Journal Title

      有機合成化学協会誌 62・7

      Pages: 693-704

    • Related Report
      2004 Annual Research Report
  • [Journal Article] New Synthesis of (-)- and (+)-Actinobolin from D-Glucose2003

    • Author(s)
      Satoshi Imuta
    • Journal Title

      Tetrahedron Letters 44・27

      Pages: 5047-5051

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] (+)-(1S,2S,4S,4aR,5R,6S,9S,10S)-4-Benzyloxy-9,10-(carbonyldioxy)-1-methoxymethoxy-4a,6,8,8-tetramethyl-7-methyl enedodecahydro-6,9-ethanobenzocyclooctene-5-o12003

    • Author(s)
      Shigeru Ohba
    • Journal Title

      Acta Crystallographica Section E E59

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] New Synthesis of (-)-and (+)-Actinobolin from D-Glucose2003

    • Author(s)
      Satoshi Imuta
    • Journal Title

      Tetrahedron Letters 44

      Pages: 5047-5051

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] (+)-(1S,2S,4S,4aR,5R,6S,9S,10S)-4-Benzyloxy-9,10-(carbonyldioxy) 1-methoxymethoxy-4a,6,8,8-tetramethy1-7-methylenedodecahydro- 6,9-ethanobenzocyclooctene-5-ol2003

    • Author(s)
      Shigeru Ohba
    • Journal Title

      Acta Crystallographica Section E E59

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] (+)-(1S,2S,4S,4aS,5R,6S,9S,10S)-4-Benzyloxy-9,10-(carbonyldioxy)-1-methoxy-methoxy-4a,6,8,8-tetramethyl-7-methylenedodecahydro-6,9-ethanobenzocyclooctene-5-ol2003

    • Author(s)
      Shigeru Ohba
    • Journal Title

      Acta Crystallographica Section E E59

    • Related Report
      2004 Annual Research Report
  • [Publications] S.Imuta: "New Synthesis of (-)- and (+)-Actinobolin from D-Glucose"Tetrahedron Letters. 44・27. 5047-5051 (2003)

    • Related Report
      2003 Annual Research Report

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Published: 2003-04-01   Modified: 2016-04-21  

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