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Stereocontrolled synthesis

Research Project

Project/Area Number 24590034
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionKyoto Pharmaceutical University

Principal Investigator

UENISHI Jun'ichi  京都薬科大学, 薬学部, 教授 (50167285)

Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2014: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2013: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2012: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywordsゴニオシン / 天然物合成 / Pd触媒反応 / アセトゲニン / 不斉合成 / 立体化学 / 薬学 / 生物活性 / 合成化学 / 1,3-不斉転写 / 抗がん活性 / パラジウム触媒
Outline of Final Research Achievements

Acetogenin is a class of polyketides of natural product obtained from Annonaceous plants. Although they exhibit diverse bioactivities, potent antitumor activity has particular attracted. Goniocin was isolated from a bark part of Goniothalamus giganteus in Thailand and has exhibited potent cytotoxic activity against several tumor cell lines at a level of nano molar. Goniocin is only a natural compound to possess a contiguous all trans-tris-THF ring system that consists of trans-threo-trans-threo-trans stereochemistry. In this research, the chemical total synthesis of this natural product has been accomplished.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (22 results)

All 2015 2014 2013 2012 Other

All Journal Article (9 results) (of which Peer Reviewed: 8 results,  Open Access: 5 results,  Acknowledgement Compliant: 5 results) Presentation (12 results) Remarks (1 results)

  • [Journal Article] Hydroxy group directed stereochemistry in oxypalladation of chiral allylic alcohol2015

    • Author(s)
      Ida, Akiko; Kitao, Kazuyuki; Hoshiya, Naoyuki; Uenishi, Jun'ichi
    • Journal Title

      Tetrahedron Letters

      Volume: 56 Issue: 15 Pages: 1956-1959

    • DOI

      10.1016/j.tetlet.2015.02.053

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Investigation of Pd(II)-catalyzed cyclization of chiral θ-hydroxy-α,β,γ,δ-unsaturated dienol2015

    • Author(s)
      Akiko Ida, Naoyuki Hoshiya, and Jun’ichi Uenishi
    • Journal Title

      Heterocycles

      Volume: 90 Issue: 2 Pages: 1082-1093

    • DOI

      10.3987/com-14-s(k)77

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Gold(I)-Catalyzed Asymmetric Desymmetrization of meso-Alkynyl Diols and Kinetic Resolution of the Corresponding DL-Diols: Effects of Celite Filtration and Silver Salts2015

    • Author(s)
      Sota, Yumi; Yamamoto, Masaaki; Murai, Masato; Uenishi, Jun-ichi; Uemura, Motokazu
    • Journal Title

      Chemistry - A European Journal

      Volume: 21 Issue: 11 Pages: 4398-4404

    • DOI

      10.1002/chem.201405889

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Alkene migration to the end-terminal carbon bearing a phenyl group over a chiral siloxy carbon center in Heck reaction2015

    • Author(s)
      Ida, Akiko; Hoshiya, Naoyuki; Uenishi, Jun'ichi
    • Journal Title

      Tetrahedron

      Volume: 71 Issue: 37 Pages: 6442-6448

    • DOI

      10.1016/j.tet.2015.03.018

    • Related Report
      2014 Annual Research Report
    • Acknowledgement Compliant
  • [Journal Article] Synthesis of optically pure (R)- and (S)-tetrahydroisoquinoline-1- and -3-carboxylic acids2015

    • Author(s)
      Kurata, Kaoruko; Inoue, Kumiko; Nishimura, Kazuhiko; Hoshiya, Naoyuki; Kawai, Nobuyuki; Uenishi, Junichi
    • Journal Title

      Synthesis

      Volume: 47 Issue: 09 Pages: 1238-1244

    • DOI

      10.1055/s-0034-1380289

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Synthesis and Cytotoxic Activity of N,N’-Arylmethylidenbisamide2015

    • Author(s)
      Jun’ichi Uenishi, Hirokazu Hirano, Tsuyoshi, Ueda, Naoyuki Hoshiya, Hiromi Ii, Tatsuhiro Yoshiki
    • Journal Title

      Synthesis

      Volume: 47

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Stereoselective synthesis of contiguous THF-THF and THF-THP units via PdII-catalyzed tandem reaction with 1,3-chirality transfer2013

    • Author(s)
      Nobuyuki Kawai, Yuhei Fujikura, Jun’ichi Takita, Jun’ichi Uenishi
    • Journal Title

      Tetrahedron

      Volume: 69 Issue: 51 Pages: 11017-11024

    • DOI

      10.1016/j.tet.2013.09.067

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Stereochemistry and Synthetic Applications of Intramolecular Chirality Transfer Reaction Promoted by Pd<sup>II</sup>-catalyst2013

    • Author(s)
      上西潤一、河井伸之
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 71 Issue: 9 Pages: 912-925

    • DOI

      10.5059/yukigoseikyokaishi.71.912

    • NAID

      10031196513

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis and Biological Evaluation of (-)-Apicularen A and its Analogues2012

    • Author(s)
      Sanjay S.Palimkar, Jun'ichi Uenishi, Hitomi Ii
    • Journal Title

      J.Org.Chem.

      Volume: 77 Issue: 1 Pages: 388-399

    • DOI

      10.1021/jo2019762

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] THF環に隣接したホルミル基へのGrignard試薬による求核付加の立体化学2014

    • Author(s)
      佐々木舞、鈴木 愛、上田 毅、加藤夕佳、星谷尚亨、上西潤一
    • Organizer
      第3回創薬科学フロンティアシンポジウム
    • Place of Presentation
      京都
    • Year and Date
      2014-11-22 – 2014-11-23
    • Related Report
      2014 Annual Research Report
  • [Presentation] テトラヒドロフラン環2位置換ホルミル基に対する求核付加反応とその立体化学2014

    • Author(s)
      鈴木 愛、佐々木舞、上田 毅、星谷尚亨、上西潤一
    • Organizer
      第40回反応と合成の進歩シンポジウム
    • Place of Presentation
      仙台
    • Year and Date
      2014-11-10 – 2014-11-11
    • Related Report
      2014 Annual Research Report
  • [Presentation] THF環に隣接したホルミル基への立体選択的求核付加2014

    • Author(s)
      佐々木舞、鈴木愛、上田毅、加藤夕佳、星谷尚亨、上西潤一
    • Organizer
      第34回有機合成若手セミナー
    • Place of Presentation
      大阪
    • Year and Date
      2014-08-05
    • Related Report
      2014 Annual Research Report
  • [Presentation] Heck反応における異常zipper現象とそのメカニズム2014

    • Author(s)
      井田安紀子、上西潤一
    • Organizer
      第105回有機合成シンポジウム2014年
    • Place of Presentation
      東京
    • Year and Date
      2014-06-10 – 2014-06-11
    • Related Report
      2014 Annual Research Report
  • [Presentation] アルケニル基から2,5-trans THF環への変換プロセスの改良とcyclogoniodenin Tの合成2013

    • Author(s)
      鈴木 愛、仲岸哲也、河井伸之、上西潤一
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2013 Research-status Report
  • [Presentation] 2価Pd触媒を用いる分子内 oxypalladation の立体化学2013

    • Author(s)
      村田裕基、上西潤一
    • Organizer
      第33回有機合成若手セミナー
    • Place of Presentation
      神戸
    • Related Report
      2013 Research-status Report
  • [Presentation] Pd(II)-catalyzed tandem reaction for a construction of bis-THF rings2013

    • Author(s)
      Nobuyuki Kawai, Yuhei Fujikura, Jun’ichi Uenishi
    • Organizer
      The 24th International Society of Heterocyclic Chemistry Congress
    • Place of Presentation
      Shanhai
    • Related Report
      2013 Research-status Report
  • [Presentation] Pd触媒を用いる2,5- 二置換テトラヒドロフラン環形成反応2013

    • Author(s)
      村田裕基、上西潤一
    • Organizer
      第39回反応と合成の進歩シンポジウム
    • Place of Presentation
      福岡
    • Related Report
      2013 Research-status Report
  • [Presentation] アルケニル基から2,5-trans THF環への変換プロセスの改良とgoniocinの合成2013

    • Author(s)
      鈴木愛、仲岸哲也、河井伸之、上西潤一
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Research-status Report
  • [Presentation] 連続するbisおよびtrisTHF環の立体化学を制御した構築;Cyclogoniodenin-Tおよびgoniocinの合成研究2012

    • Author(s)
      河井伸之、仲岸哲也、藤倉悠平、鈴木愛、Vijaykumar Shivdas More, 上西潤一
    • Organizer
      第38回反応と合成の進歩シンポジウム講演
    • Place of Presentation
      東京
    • Related Report
      2012 Research-status Report
  • [Presentation] 連続するbis-THF環の立体選択的合成2012

    • Author(s)
      仲岸哲也、鈴木愛、河井伸之、上西潤一
    • Organizer
      第39回会有機反応懇談会
    • Place of Presentation
      大阪
    • Related Report
      2012 Research-status Report
  • [Presentation] 抗がん活性アセトゲニン天然化合物goniocinの全合成研究2012

    • Author(s)
      鈴木愛、仲岸哲也、上西潤一
    • Organizer
      第32回有機合成若手セミナー
    • Place of Presentation
      神戸
    • Related Report
      2012 Research-status Report
  • [Remarks] 京都薬科大学薬化学分野

    • URL

      http://www.kyoto-phu.ac.jp/labo/yakka/

    • Related Report
      2012 Research-status Report

URL: 

Published: 2013-05-31   Modified: 2019-07-29  

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