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Synthetic study of estrone derivatives based on new method for generation of o-quinodimethane species

Research Project

Project/Area Number 18590002
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

KITAGAKI Shinji  Kanazawa University, 薬学系, 准教授 (20281818)

Co-Investigator(Kenkyū-buntansha) MUKAI Chisato  金沢大学, 薬学系, 教授 (70143914)
Project Period (FY) 2006 – 2008
Project Status Completed (Fiscal Year 2008)
Budget Amount *help
¥4,100,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥600,000)
Fiscal Year 2008: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2007: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2006: ¥1,500,000 (Direct Cost: ¥1,500,000)
Keywords合成化学 / オルトキノジメタン / エンジアレン / タンデム環化 / エストロン / [4+2]環化付加 / 光延反応 / プロパルギルアルコール
Research Abstract

女性ホルモンの一種であり多種多様な薬理作用を示すことが知られているエストロンやその関連化合物の一般合成法を開発すべく, 筆者らが最近見出した新規なエン-ジアレン形成に基づくオルトキノジメタン発生法を活用した上記化合物の合成研究を行った。その結果, 穏和な条件下でのステロイド骨格構築法を開発し, ラセミのエストロンの全合成を達成した。また, アレンを利用した各種環状化合物の合成法を見出すことにも成功した。

Report

(4 results)
  • 2008 Annual Research Report   Final Research Report ( PDF )
  • 2007 Annual Research Report
  • 2006 Annual Research Report
  • Research Products

    (29 results)

All 2009 2008 2007 2006

All Journal Article (18 results) (of which Peer Reviewed: 15 results) Presentation (11 results)

  • [Journal Article] アレンと多重結合間の分子内付加環化反応2009

    • Author(s)
      北垣伸治, 稲垣冬彦, 向智里
    • Journal Title

      有機合成化学協会誌 67

      Pages: 6-6

    • NAID

      10024969415

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium (I) -Catalyzed Intramolecular Carbonylative[2+2+1]Cycloaddition of Bis(allene)s : Bicyclo[6. 3. 0]undecadienones and Bicyclo[5. 3. 0]decadienones2009

    • Author(s)
      F. Inagaki, S. Narita, T. Hasegawa, S. Kitagaki, C. Mukai
    • Journal Title

      Angew. Chem. Int. Ed 48

      Pages: 2007-2011

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium (I)-catalyzed Intramolecular Carbonylative [2+2+1] Cycloaddition of Bis (allene) s : Bicyclo [6.3.0] undecadienones and Bicyclo [5.3.0] decadienones2009

    • Author(s)
      F. Inagaki
    • Journal Title

      Angew. Chem. Int. Ed. 48

      Pages: 2007-2011

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Investigation of Oxacycle Formation by Base-Promoted Endo-Mode Ring-Closing Reaction of Allenes2008

    • Author(s)
      S. Kitagaki, T. Kawamura, D. Shibata, C. Mukai
    • Journal Title

      Tetrahedron 64

      Pages: 11086-11095

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Investigation of Oxacycle Formation by Base-promoted Endo-mode Ring-closing Reaction of Allenes2008

    • Author(s)
      S. Kitagaki
    • Journal Title

      Tetrahedron 64

      Pages: 11086-11095

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Sequential Pericyclic Reaction of Ene-diallene : Synthesis of(±)-Estrone2007

    • Author(s)
      H. Hakuba, S. Kitagaki, C. Mukai
    • Journal Title

      Tetrahedron 63

      Pages: 12639-12645

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Ring-Closing Reaction of Allenic/Propargylic Anions Generated by Base Treatment of Sulfonylallenes2007

    • Author(s)
      S. Kitagaki, S. Teramoto, C. Mukai
    • Journal Title

      Org. Lett. 9

      Pages: 2549-2552

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Studies of Ring-Closing Mode of 4-Hydroxy-2-vinylidenebutanoates : 5-Exo-trig versus 5-Endo-dig2007

    • Author(s)
      S. Kitagaki, D. Shibata, C. Mukai
    • Journal Title

      Tetrahedron Lett. 48

      Pages: 1735-1738

    • NAID

      120000809613

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Sequential Pericyclic Reaction of Ene-diallene: Synthesis of (±)-Estrone2007

    • Author(s)
      H. Hakuba
    • Journal Title

      Tetrahedron 63

      Pages: 12639-12645

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ring-closing Reaction of Allenic/propargylic Anions Generated by Base Treatment of Sulfonylallenes2007

    • Author(s)
      S. Kitagaki
    • Journal Title

      Organic Letters 9

      Pages: 2549-2552

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Studies of Ring-closing Mode o f4-Hydroxy-2-vinylidenebutanoates: 5-Exo-trigversus 5-Endo-dig2007

    • Author(s)
      S. Kitagaki
    • Journal Title

      Tetrahedron Letters 48

      Pages: 1735-1738

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Reaction of Ene-bis(phosphinylallenes) : [2+2]versus[4+2]Cycloaddition2006

    • Author(s)
      S. Kitagaki, Y. Okumura, C. Mukai
    • Journal Title

      Tetrahedron 62

      Pages: 10311-10320

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Intermolecular[4+2]Cycloaddition of o-Quinodimethanes Derived from Ene-bis(sulfinylallenes)2006

    • Author(s)
      S. Kitagaki, K. Katoh, K. Ohdachi, Y. Takahashi, D. Shibata, C. Mukai
    • Journal Title

      J. Org.Chem. 71

      Pages: 6908-6914

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Naphtho[b]cyclobutenes from1, 2-Bis (3-propynol) benzenes2006

    • Author(s)
      S. Kitagaki, Y. Okumura, C. Mukai
    • Journal Title

      Tetrahedron Lett. 47

      Pages: 1849-1852

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Sequential Pericyclic Reaction of Ene-diallenes : An Efficient Approach to the Steroid Skeleton2006

    • Author(s)
      S. Kitagaki, K. Ohdachi, K. Katoh, C. Mukai
    • Journal Title

      Org. Lett. 8

      Pages: 95-98

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Reaction of Ene-bis(phosphinylallenes) : [2+2]versus[4+2]Cycloaddition2006

    • Author(s)
      S.Kitagaki
    • Journal Title

      Tetrahedron 62

      Pages: 10311-10320

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Intermolecular [4+2] Cycloaddition of ο-Quinodimethanes Derived from Ene-bis(sulfinylallenes).2006

    • Author(s)
      S.Kitagaki
    • Journal Title

      J.Org.Chem. 71

      Pages: 6908-6914

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Synthesis of Naphtho[b]cyclobutenes from 1,2-Bis(3-propynol)benzenes2006

    • Author(s)
      S.Kitagaki
    • Journal Title

      Tetrahedron Lett. 47

      Pages: 1849-1852

    • Related Report
      2006 Annual Research Report
  • [Presentation] スルホニル置換ビスアレン体を用いたビシクロ[6. 3. 0]骨格の構築2009

    • Author(s)
      北垣伸治
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      国立京都国際会館, 京都
    • Year and Date
      2009-03-28
    • Related Report
      2008 Annual Research Report
  • [Presentation] スルホニル置換ビスアレン体を用いたビシクロ[6. 3. 0]骨格の構築2009

    • Author(s)
      稲垣冬彦, 成田集, 長谷川琢真, 北垣伸治, 向智里
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都
    • Related Report
      2008 Final Research Report
  • [Presentation] アレンを活用したラクトン環構築の検討2008

    • Author(s)
      向智里, 川村行正, 北垣伸治
    • Organizer
      日本薬学会第128年会
    • Place of Presentation
      横浜
    • Related Report
      2008 Final Research Report
  • [Presentation] アレニル/プロパルギルアニオンの閉環反応2008

    • Author(s)
      向智里, 宮下祐輔, 北垣伸治
    • Organizer
      日本薬学会第128年会
    • Place of Presentation
      横浜
    • Related Report
      2008 Final Research Report
  • [Presentation] ビスアレンのPauson-Khand 型反応2008

    • Author(s)
      向智里, 成田集, 長谷川琢真, 北垣伸治
    • Organizer
      日本薬学会第128年会
    • Place of Presentation
      横浜
    • Related Report
      2008 Final Research Report
  • [Presentation] エンジアレン中間体の連続的環化反応を用いたエストロンの合成2007

    • Author(s)
      白馬 弘文
    • Organizer
      有機合成化学北陸セミナー
    • Place of Presentation
      金沢商工会議所会館,金沢,石川
    • Year and Date
      2007-10-12
    • Related Report
      2007 Annual Research Report
  • [Presentation] Studies of Ring-closing Mode: Exo-trig versus Endo-dig2007

    • Author(s)
      S. Kitagaki
    • Organizer
      21st International Congress for Heterocyclic Chemistry
    • Place of Presentation
      The University of New South Wales,Sydney,Australia
    • Year and Date
      2007-07-19
    • Related Report
      2007 Annual Research Report
  • [Presentation] エンジアレン中間体の連続的環化反応を用いたエストロンの合成2007

    • Author(s)
      白馬弘文, 北垣伸治, 向智里
    • Organizer
      平成19年度有機合成化学北陸セミナ-
    • Place of Presentation
      金沢
    • Related Report
      2008 Final Research Report
  • [Presentation] エチレン鎖で連結した1, 4-ビスアレンの環化付加反応2007

    • Author(s)
      北垣伸治, 成田集, 向智里
    • Organizer
      平成19年度有機合成化学北陸セミナ-
    • Place of Presentation
      金沢
    • Related Report
      2008 Final Research Report
  • [Presentation] Studies of Ring-Closing Mode : Exo-Trig versus Endo-Dig2007

    • Author(s)
      S. Kitagaki, D. Shibata, C. Mukai
    • Organizer
      21th International Congress of Heterocyclic Chemistry
    • Place of Presentation
      Sydney, Australia
    • Related Report
      2008 Final Research Report
  • [Presentation] 4-Hydroxy-2-vinylidenebutanoate の閉環反応における位置選択性 : 5-exo-trig vs5-endo-dig2007

    • Author(s)
      北垣伸治, 柴田大助, 向智里
    • Organizer
      日本薬学会第127年
    • Place of Presentation
      富山
    • Related Report
      2008 Final Research Report

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

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