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Deve I opment of Practical Radical Reaction and its Applicat i on to the Synthesis of Physiologically Active Compounds

Research Project

Project/Area Number 16390004
Research Category

Grant-in-Aid for Scientific Research (B)

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

Principal Investigator

ISHIBASHI Hiroyuki  Graduate School of Natural Science and Technology., Professor, 自然科学研究科, 教授 (70028869)

Co-Investigator(Kenkyū-buntansha) UCHIYAMA Masahiko  Advanced Science Research Center., Associate Professor, 学際科学実験センター, 助教授 (40277265)
MATSUO Jun-ichi  Graduate School of Natural Science and Technology, Associate Professor, 自然科学研究科, 助教授 (50328580)
田村 修  金沢大学, 自然科学研究科, 助教授 (30257141)
Project Period (FY) 2004 – 2006
Project Status Completed (Fiscal Year 2006)
Budget Amount *help
¥13,700,000 (Direct Cost: ¥13,700,000)
Fiscal Year 2006: ¥4,200,000 (Direct Cost: ¥4,200,000)
Fiscal Year 2005: ¥4,600,000 (Direct Cost: ¥4,600,000)
Fiscal Year 2004: ¥4,900,000 (Direct Cost: ¥4,900,000)
Keywordsenamide / radical cyclization / stemonamide / radical cascade / single electron transfer / lennoxamine / cylindricine / cephalotaxine / ピロリジジンアルカロイド / ラジカル / 環化反応 / 位置化学 / 環状化合物 / トリブチルスズ / ラジカル反応 / アゾビスイソブチロニトリル / シリンドリシン / ラクタム / イソニトリル / 酢酸(III)マンガン / グループトランスファー / 一電子還元
Research Abstract

1. Radical cascade involving 6-endo selective cyclization of aryl radical onto olefinic bond of enamide and 5-endo cyclization of the resulting amidoyl radical afforded a convenient synthesis of phenanthroindolizidines containing a methyl group at their C13 position.
2. Radical cascade involving 6-endo selective cyclization of alkyl radical onto olefinic bond of enamide and 5-endo cyclization of the resulting amidoyl radical afforded a convenient synthesis of cylindricine skeleton.
3. Radical cascade involving 7-endo selective cyclization of aryl radical onto olefinic bond of enamide and 5-endo cyclization of the resulting amidoyl radical afforded a concise synthesis of cephalotoxine skeleton.
4. Radical cascade involving 7-endo selective cyclization of aryl radical onto olefinic bond of enamide and homolytic aromatic substitution of the resulting amidoyl radical afforded a short synthesis of lennoxamine.
5. Radical cascade involving 7-endo selective cyclization of alkyl radical onto olefinic bond of enamide and 5--endo cyclization of the resulting amidoyl radical afforded a total synthesis of stemonamide, isostemonamide, stemonamine, and isostemonamine.
6. N-Allylic or N-vinylic, α, α, α-trichloroacetamides, upon heating in 1, 4-dimethylpiperazine, underwent radical cyclization to give the corresponding y-lactams.
7. exo and endo Selectivities of aryl or alkyl radical onto olefinic bond of enamides were studied in detail.

Report

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

    (23 results)

All 2006 2005 2004 Other

All Journal Article (23 results)

  • [Journal Article] Controlling the Regiochemistry of Radical Cyclizations2006

    • Author(s)
      Hiroyuki Ishibashi
    • Journal Title

      Chem. Rec. 6・1

      Pages: 23-31

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Radical Cyclizations in 1,4-Dimethylpiperazine2006

    • Author(s)
      Hiroyuki Ishibashi
    • Journal Title

      Tetrahedron Lett. 47・35

      Pages: 6263-6266

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Controlling the Regiochemistry of Radical Cyclizations2006

    • Author(s)
      Hiroyuki Ishibashi
    • Journal Title

      Chem. Rec. 6-1

      Pages: 23-31

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Radical Cyclizations in 1,4-Dimethylpiperazine2006

    • Author(s)
      Hiroyuki Ishibashi
    • Journal Title

      Tetrahedron Lett. 47-35

      Pages: 6263-6266

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Radical Cyclizations in 1,4-Dimethylpiperazine2006

    • Author(s)
      Hiroyuki Ishibashi
    • Journal Title

      Tetrahedron Letters 47・35

      Pages: 6263-6266

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Stereoselective Synthesis of trans-3a-Aryloctahydroindoles Using Cyclization of N-Vinylic α-(Methylthio)acetamides2006

    • Author(s)
      Miho Saito
    • Journal Title

      Heteocycles 69

      Pages: 69-72

    • Related Report
      2006 Annual Research Report
  • [Journal Article] 7-endo Selective Aryl Radical Cyclization onto Enamides Leading to 3-Benzazepines : Concise Construction of a Cephalotaxine Skeleton2005

    • Author(s)
      Tsuyoshi Taniguchi
    • Journal Title

      J. Org. Chem. 70・5

      Pages: 1922-1925

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Concise Synthesis of the Tricyclic Skeleton of Cylindricines Using a Radical Cascade Involving 6-Endo Selective Cyclization2005

    • Author(s)
      Tsuyoshi Taniguchi
    • Journal Title

      Synlett 2005・7

      Pages: 1179-1181

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Bu_3SnH-Mediated 5-Exo Selective Radical Cyclization of N-Vinyl-α,β-Unsaturated Amides Leading to γ-Lactams2005

    • Author(s)
      Takashi Okitsu
    • Journal Title

      Tetrahedron 61・38

      Pages: 9180-9187

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary 2005 Annual Research Report
  • [Journal Article] A Short Synthesis of Lennoxamine Using a Radical Cascade2005

    • Author(s)
      Tsuyoshi Taniguchi
    • Journal Title

      Org. Lett. 7・20

      Pages: 4389-4390

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] 7-endo Selective Aryl Radical Cyclization onto Enamides Leading to 3-Benzazepines : Concise Construction of a Cephalotaxine Skeleton2005

    • Author(s)
      Tsuyoshi Taniguchi
    • Journal Title

      J. Org. Chem. 70-5

      Pages: 1922-1925

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Concise Synthesis of the Tricyclic Skeleton of Cylindricines Using a Radical Cascade Involving 6-Endo Selective Cyclization2005

    • Author(s)
      Tsuyoshi Taniguchi
    • Journal Title

      Synlett 2005-7

      Pages: 1179-1181

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Bu3SnH-Mediated 5-Exo Selective Radical Cyclization of N-Vinyl-α,β-Unsaturated Amides Leading to y-Lactams2005

    • Author(s)
      Takashi Okitsu
    • Journal Title

      Tetrahedron 61-38

      Pages: 9180-9187

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] A Short Synthesis of Lennoxamine Using a Radical Cascade2005

    • Author(s)
      Tsuyoshi Taniguchi
    • Journal Title

      Org. Lett. 7-20

      Pages: 4389-4390

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] 7-Endo Selective Aryl Radical Cyclization onto Enamides Leading to 3-Benzazepines : Concise Construction of a Cephalotaxine Skeleton2005

    • Author(s)
      Tsuyoshi Taniguchi
    • Journal Title

      The Journal of Organic Chemistry 70・5

      Pages: 1922-1925

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Concise Synthesis of the Tricyclic Skeleton of Cylindricines Using a Radical Cascade Involving 6-Endo Selective Cyclization2005

    • Author(s)
      Tsuyoshi Taniguchi
    • Journal Title

      Synlett 1005・7

      Pages: 1179-1181

    • Related Report
      2005 Annual Research Report
  • [Journal Article] A Short Synthesis of Lennoxamine Using a Radical Cascade2005

    • Author(s)
      Tsuyoshi Taniguchi
    • Journal Title

      Organic Letters 7・20

      Pages: 4389-4390

    • Related Report
      2005 Annual Research Report
  • [Journal Article] 7-Endo Selective Aryl Radical Cyclization onto Enamides Leading to 3-2005

    • Author(s)
      谷口剛史
    • Journal Title

      The Journal of Organic Chemistry 70・05

      Pages: 1922-1925

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Control of Regiochemistry of Radical Cyclizations and Application to the Synthesis of Physiologically Active Compounds2004

    • Author(s)
      Hiroyuki Ishibashi
    • Journal Title

      J. Synth. Org. Chem. Jpn. 62・4

      Pages: 324-334

    • NAID

      130000928782

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Control of Regiochemistry of Radical Cyclizations and Application totheSynthesis of Physiological IyActive Compounds2004

    • Author(s)
      Hiroyuki Ishibashi
    • Journal Title

      J. Synth. Org. Chem. Jpn. 62-4

      Pages: 324-334

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] ラジカル環化反応の位置化学の制御と生理活性化合物合成への応用2004

    • Author(s)
      石橋弘行
    • Journal Title

      有機合成化学協会誌 62・04

      Pages: 324-334

    • NAID

      130000928782

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Stereoselective Synthesis of cis and trans-Fused 3a-Arylocta-hydroindoles Using Cyclization of N-Vinylic α-(Methylthio)-acetamides : Synthesis of (-)-Mesembrane

    • Author(s)
      Miho Saito
    • Journal Title

      Tetrahedron (印刷中)

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Controlling the Regiochemistry of Radical Cyclizations

    • Author(s)
      Hiroyuki Ishibashi
    • Journal Title

      The Chemical Record (印刷中)

    • Related Report
      2005 Annual Research Report

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Published: 2004-04-01   Modified: 2016-04-21  

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