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Synthetic Study of Antitumor Alkaloids Haouamines Using a Cascade Cyclization

Research Project

Project/Area Number 21790011
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

TANIGUCHI Tsuyoshi  Kanazawa University, 薬学系, 助教 (60444204)

Project Period (FY) 2009 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
Fiscal Year 2010: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2009: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywordsカスケード反応 / 溝呂木-ヘック反応 / プメラー型反応 / 全合成 / ハオウアミン / ラジカル反応 / 鉄触媒
Research Abstract

Formal synthesis of haouamine A has been achieved using cascade Mizoroki-Heck cyclization to give an indenotetrahydropyridine core. On the other hand, synthesis of a core of haouamine B using Pummerer-type cyclizations was difficult. However, this synthetic study gave us an opportunity to develop a new methodology such as iron-catalyzed radical reactions using hydrazine compounds and nitration reactions of alkenes.

Report

(3 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • Research Products

    (17 results)

All 2011 2010 2009 Other

All Journal Article (12 results) (of which Peer Reviewed: 12 results) Presentation (3 results) Remarks (2 results)

  • [Journal Article] Iron-catalyzedsulfonyl radical formations from sulfonylhydrazides and oxidative addition to alkenes.2011

    • Author(s)
      Tsuyoshi Taniguchi, Atsushi Idota, Hiroyuki Ishibashi
    • Journal Title

      Org.Biomol.Chem. 9

      Pages: 3151-3153

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] A Mild Oxidative ArylRadical Addition into Alkenes withAerobic Oxidation of Arylhydrazines.2011

    • Author(s)
      Tsuyoshi Taniguchi, Hisaaki Zaimoku, Hiroyuki Ishibashi
    • Journal Title

      Chem.Eur.J. 17

      Pages: 4307-4312

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Iron-mediatedone-pot formal nitrocyclization ontounactivated alkenes.2011

    • Author(s)
      Tsuyoshi Taniguchi, Tatsuya Fujii, Hiroyuki Ishibashi
    • Journal Title

      Org.Biomol.Chem. 9

      Pages: 653-655

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Iron-mediated one-pot formal nitrocyclization onto unactivated alkencs2011

    • Author(s)
      Tsuyoshi Taniguchi, et al.
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 9 Pages: 653-655

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Mild Oxidative Aryl Radical Addition into Alkenes with Aerobic Oxidation of Arylhydrazines2011

    • Author(s)
      Tsuyoshi Taniguchi, et al.
    • Journal Title

      Chemistry-A European Journal

      Volume: 17 Pages: 4307-4312

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iron-catalyzed sulfonyl radical formations from sullonylhydrazides and oxidative addition to alkenes2011

    • Author(s)
      Tsuyoshi Taniguchi, et al.
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 9(In press)

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iron-Catalyzed Oxidative Addition ofAlkoxycarbonyl Radicals to Alkenes withCarbazates and Air.2010

    • Author(s)
      Tsuyoshi Taniguchi, Yuki Sugiura, Hisaaki Zaimoku, Hiroyuki Ishibashi
    • Journal Title

      Angew.Chem., Int.Ed. 49

      Pages: 1015-10157

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Iron-MediatedRadical Halo-Nitration of Alkenes.2010

    • Author(s)
      Tsuyoshi Taniguchi, Tatsuya Fujii, Hiroyuki Ishibashi
    • Journal Title

      J.Org.Chem. 75

      Pages: 8126-8132

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Iron-Mediated Radical Halo-Nitration of Alkenes2010

    • Author(s)
      Tsuyoshi Taniguchi, et al.
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 75 Pages: 8126-8132

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iron-Catalyzed Oxidative Addition of Alkoxycarbonyl Radicals to Alkenes with Carbazates and Air2010

    • Author(s)
      Tsuyoshi Taniguchi, et al.
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 49 Pages: 10154-10157

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Formal TotalSynthesis of Haouamine A.2009

    • Author(s)
      Tsuyoshi Taniguchi, Hisaaki Zaimoku, Hiroyuki Ishibashi
    • Journal Title

      J.Org.Chem. 74

      Pages: 2624-2626

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Formal Total Synthesis of Haouamine A2009

    • Author(s)
      Tsuyoshi Taniguchi
    • Journal Title

      The Journal of Organic Chemistry 74

      Pages: 2624-2626

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] 亜硝酸エステルを用いるオレフィンへの簡便なニトロ化反応の開発2010

    • Author(s)
      八島淳, 谷口剛史, 石橋弘行
    • Organizer
      第36回反応と合成の進歩シンポジウム
    • Place of Presentation
      ウインクあいち(愛知県)
    • Year and Date
      2010-11-02
    • Related Report
      2010 Final Research Report
  • [Presentation] 亜硝酸エステルを用いるオレフィンへの簡便なニトロ化反応の開発2010

    • Author(s)
      八島淳, 他
    • Organizer
      第36回反応と合成の進歩シンポジウム
    • Place of Presentation
      ラインクあいち(愛知県)
    • Year and Date
      2010-11-02
    • Related Report
      2010 Annual Research Report
  • [Presentation] 鉄触媒とヒドラジン化合物を用いるオレフィンへの酸化的ラジカル付加反応2010

    • Author(s)
      谷口剛史, 材木久晃, 杉浦祐基, 井戸田淳, 横山慎一, 石橋弘行
    • Organizer
      第8回次世代を担う有機化学シンポジウム
    • Place of Presentation
      日本薬学会長井記念ホール(東京都)
    • Year and Date
      2010-05-14
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Remarks] ホームページ等

    • URL

      http://www.p.kanazawa-u.ac.jp/~gousei/

    • Related Report
      2010 Final Research Report
  • [Remarks]

    • URL

      http://www.p.kanazawa-u.ac.jp/~gousei/

    • Related Report
      2010 Annual Research Report

URL: 

Published: 2009-04-01   Modified: 2016-04-21  

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