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Convergent Synthesis of Biologically Active Natural Products via Segment Coupling Involving Ether Ring Formation

Research Project

Project/Area Number 25410118
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionOkayama University

Principal Investigator

KADOTA Isao  岡山大学, 自然科学研究科, 教授 (30250666)

Co-Investigator(Renkei-kenkyūsha) TAKAMURA Hiroyoshi  岡山大学, 大学院自然科学研究科, 助教 (70422798)
Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2013: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords全合成 / 海洋産天然物 / ポリ環状エーテル / 分子内アリル化 / 閉環メタセシス / シガトキシン / ダクチロライド / エニグマゾール / タムラミド
Outline of Final Research Achievements

Secondary metabolites produced by marine organism have been recognized as novel read compounds for new drag due to their potent bioactivities. However, because of the limited availability from nature, chemical synthesis has been required to obtain sufficient amounts of these compounds. Moreover, the unusual structures are particularly attractive targets for synthetic chemists. In this study, synthesis of these marine natural products was investigated by using convergent synthetic methodology based on intramolecular allylation.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (41 results)

All 2015 2014 2013

All Journal Article (8 results) (of which Peer Reviewed: 8 results,  Open Access: 1 results,  Acknowledgement Compliant: 2 results) Presentation (33 results) (of which Int'l Joint Research: 6 results,  Invited: 4 results)

  • [Journal Article] Stereodivergent Synthesis and Relative Stereostructure of the C1-C13 Fragment of Symbiodinolide2015

    • Author(s)
      Hiroyoshi Takamura, Hiroko Wada, Mao Ogino, Takahiro Kikuchi, Isao Kadota, Daisuke Uemura
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 80 Issue: 6 Pages: 3111-3123

    • DOI

      10.1021/acs.joc.5b00027

    • NAID

      120006522866

    • Related Report
      2015 Annual Research Report 2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Convergent Synthesis of the EFGH Ring System of Ciguatoxin CTX3C2015

    • Author(s)
      I. Kadota, Y. Sato, N. Fujita, H. Takamura, Y. Yamamoto
    • Journal Title

      Tetrahedron

      Volume: 71 Issue: 37 Pages: 6547-6558

    • DOI

      10.1016/j.tet.2015.04.106

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Improved Synthesis of the A-E Ring Segment of Ciguatoxin CTX3C2014

    • Author(s)
      Shiroma, K.; Asakura, H.; Tanaka, T.; Takamura, H.; Kadota, I.
    • Journal Title

      Heterocycles

      Volume: 88 Issue: 2 Pages: 969-973

    • DOI

      10.3987/com-13-s(s)106

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled Synthesis of the CI-C7 Fragment of Enigmazole A2014

    • Author(s)
      Takayuki Kishi, Yuka Fujisawa, Hiroyoshi Takamura, and Isao Kadota
    • Journal Title

      Heterocycles

      Volume: 89 Issue: 2 Pages: 515-522

    • DOI

      10.3987/com-13-12905

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] 造解明を指向したポリオール天然物シンビオジノライドの合成研究2014

    • Author(s)
      髙村浩由、門田功、上村大輔
    • Journal Title

      有機合成化学協会誌

      Volume: 72 Pages: 2-13

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis, Structural Elucidation, and Structure–Cytotoxic Activity Relationship of (–)-Gummiferol2013

    • Author(s)
      Hiroyoshi Takamura, Hiroko Wada, Nan Lu, Osamu Ohno, Kiyotake Suenaga, Isao Kadota
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 78 Issue: 6 Pages: 2443-2454

    • DOI

      10.1021/jo302665c

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Two Possible Diastereomers of (+)-Sarcophytonolide C and Its Structural Elucidation2013

    • Author(s)
      Total Synthesis of Two Possible Diastereomers of (+)-Sarcophytonolide C and Its Structural Elucidation
    • Journal Title

      Org. Lett

      Volume: 15 Issue: 5 Pages: 1108-1111

    • DOI

      10.1021/ol400157s

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Synthesis of the C79-C97 Fragment of Symbiodinolide2013

    • Author(s)
      Hiroyoshi Takamura, Takayuki Fujiwara, Isao Kadota, Daisuke Uemura
    • Journal Title

      Beilstein Journal of Organic Chemistry

      Volume: 9 Pages: 1931-1935

    • DOI

      10.3762/bjoc.9.228

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] Convergent Approach to the Synthesis of Ciguatoxin CTX3C2015

    • Author(s)
      I. Kadota
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2015-12-19
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Unified Total Synthesis and Biological Activity of Sarcophytonolides2015

    • Author(s)
      H. Takamura, K. Iwamoto, E. Nakao, N. Harada, T. Kikuchi, O. Ohno, K. Suenaga, N. Endo, Y. Fukuda, and I. Kadota
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2015-12-19
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthetic Study of (–)-Dactyloride2015

    • Author(s)
      T. Tanaka, Y. Murai, H. Takamura, and I. Kadota
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2015-12-18
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Total Synthesis and Biological Activity of Sarcophytonolide H2015

    • Author(s)
      T. Kikuchi, H. Takamura, and I. Kadota
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2015-12-18
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthetic Study of Enigmazole A2015

    • Author(s)
      Y. Murai, T. Kishi, Y. Fujisawa, H. Takamura, and I. Kadota
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2015-12-18
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Convergent Synthesis of the HIJKLM Ring Segment of Ciguatoxin CTX3C2015

    • Author(s)
      T. Kimoto, S. Hara, H. Takamura, and I. Kadota
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2015-12-18
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 海洋産ポリ環状エーテルの収束的合成2015

    • Author(s)
      門田 功
    • Organizer
      大阪工業大学第1回桜花城北セミナー
    • Place of Presentation
      大阪工業大学工学部、大阪
    • Year and Date
      2015-11-17
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] (–)-Dactylolideの合成研究2015

    • Author(s)
      田中睦大,村井勇斗,髙村浩由,門田功
    • Organizer
      2015年日本化学会中国四国支部大会
    • Place of Presentation
      岡山大学津島キャンパス、岡山
    • Year and Date
      2015-11-15
    • Related Report
      2015 Annual Research Report
  • [Presentation] サルコフィトノライドHとイソサルコフィトノライドDの全合成2015

    • Author(s)
      菊地崇浩,髙村浩由,門田功
    • Organizer
      2015年日本化学会中国四国支部大会
    • Place of Presentation
      岡山大学津島キャンパス、岡山
    • Year and Date
      2015-11-15
    • Related Report
      2015 Annual Research Report
  • [Presentation] エニグマゾールAの収束的合成研究2015

    • Author(s)
      村井勇斗,岸敬之,藤澤由佳,髙村浩由,門田功
    • Organizer
      2015年日本化学会中国四国支部大会
    • Place of Presentation
      岡山大学津島キャンパス、岡山
    • Year and Date
      2015-11-15
    • Related Report
      2015 Annual Research Report
  • [Presentation] シガトキシンCTX3CのHIJKLM環部の合成研究2015

    • Author(s)
      木元琢,原翔輝,髙村浩由,門田功
    • Organizer
      2015年日本化学会中国四国支部大会
    • Place of Presentation
      岡山大学津島キャンパス、岡山
    • Year and Date
      2015-11-15
    • Related Report
      2015 Annual Research Report
  • [Presentation] スカブロライドFの合成研究2015

    • Author(s)
      勝部友哉,森下諒平,髙村浩由,門田功
    • Organizer
      2015年日本化学会中国四国支部大会
    • Place of Presentation
      岡山大学津島キャンパス、岡山
    • Year and Date
      2015-11-15
    • Related Report
      2015 Annual Research Report
  • [Presentation] シガトキシンCTX3CのEFGH環部の収束的合成研究2015

    • Author(s)
      熊本健太郎,城間賢悟,髙村浩由,門田功
    • Organizer
      2015年日本化学会中国四国支部大会
    • Place of Presentation
      岡山大学津島キャンパス、岡山
    • Year and Date
      2015-11-15
    • Related Report
      2015 Annual Research Report
  • [Presentation] サルコフィトノライド類の統一的合成と構造活性相関に関する研究2015

    • Author(s)
      髙村浩由,菊地崇浩,岩本浩平,仲尾英史,原田直樹,大野修,末永聖武,遠藤紀之,福田祐司,門田功
    • Organizer
      第57回天然有機化合物討論会
    • Place of Presentation
      神奈川県民ホール、横浜
    • Year and Date
      2015-06-11
    • Related Report
      2015 Annual Research Report
  • [Presentation] サルコフィトノライド類の統一的全合成と生物活性2015

    • Author(s)
      髙村浩由,菊地崇浩,岩本浩平,仲尾英史,原田直樹,大野修,末永聖武,遠藤紀之,福田祐司,門田功
    • Organizer
      第107回有機合成シンポジウム
    • Place of Presentation
      慶應義塾大学薬学部、東京
    • Year and Date
      2015-06-09
    • Related Report
      2015 Annual Research Report
  • [Presentation] 立体構造決定を目的とした6-クロロテトラヒドロフランアセトゲニンの合成研究2015

    • Author(s)
      岡本和樹
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学船橋キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] (–)-ダクチロライドの合成研究2015

    • Author(s)
      田中睦大
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学船橋キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] サルコフィトノライドHの全合成2015

    • Author(s)
      菊地崇浩
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学船橋キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] Convergent Approach to the Synthesis of Ciguatoxin CTX3C2015

    • Author(s)
      Isao Kadota
    • Organizer
      The 5th Annual Basic Science International Conference 2015
    • Place of Presentation
      インドネシア、マラン
    • Year and Date
      2015-02-11 – 2015-02-12
    • Related Report
      2014 Research-status Report
  • [Presentation] Synthetic Study of Tamulamide A2014

    • Author(s)
      Isao Kadota
    • Organizer
      Vietnam Malaysia International Chemical Congress (VMICC) 2014
    • Place of Presentation
      ベトナム、ハノイ
    • Year and Date
      2014-11-07 – 2014-11-10
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] Synthetic Study of Ciguatoxin CTX3C2014

    • Author(s)
      Isao Kadota
    • Organizer
      18th Malaysian International Chemical Congress (18MICC) 2014
    • Place of Presentation
      マレーシア、クアラルンプール
    • Year and Date
      2014-11-03 – 2014-11-05
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] シンビオジノライドC1–C13フラグメントの立体発散的合成と相対立体構造2014

    • Author(s)
      髙村浩由
    • Organizer
      第56回天然有機化合物討論会
    • Place of Presentation
      高知
    • Year and Date
      2014-10-15 – 2014-10-17
    • Related Report
      2014 Research-status Report
  • [Presentation] Total Synthesis of Two Possible Diastereomers of (+)-Sarcophytonolide C and Its Absolute Configurational Elucidation2014

    • Author(s)
      Hiroyoshi Takamura
    • Organizer
      International Symposia on Advancing the Chemical Sciences (ISACS) 14
    • Place of Presentation
      中国、上海
    • Year and Date
      2014-08-07 – 2014-08-10
    • Related Report
      2014 Research-status Report
  • [Presentation] タムラミドAの全合成2014

    • Author(s)
      岸敬之、原翔輝、山神雄司、藤澤由佳、高村浩由、門田功
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] シガトキシンCTX3CのABCDE環部及びEFGH環部の合成2014

    • Author(s)
      城間賢悟、朝倉大樹、乾律動、田中睦大、高村浩由、門田功
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] シンビオジノライドC94-C104フラグメントの立体発散的合成2014

    • Author(s)
      川久保陽平、藤原敬之、高村浩由、門田功、上村大輔
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] サルコフィトノライドFの全合成2014

    • Author(s)
      仲尾英史、高村浩由、門田功
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] スカブロライドFの合成研究2014

    • Author(s)
      森下諒平、高村浩由、門田功
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] シンビオジノライドC1-C13フラグメントの立体発散的合成2014

    • Author(s)
      荻野真生、和田寛子、高村浩由、門田功、上村大輔
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] (-)-Dactylolideの合成研究2014

    • Author(s)
      田中睦大、村井勇斗、高村浩由、門田功
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] 分子内アリル化を基盤としたシガトキシンCTX3Cの合成研究2013

    • Author(s)
      高村浩由、阿部享史、西馬直希、宇仁巳由紀、伊塚浩章、門田功
    • Organizer
      第103回有機合成シンポジウム
    • Place of Presentation
      慶應義塾大学薬学部
    • Related Report
      2013 Research-status Report
  • [Presentation] (-)-グンミフェロールの全合成・構造決定・構造活性相関2013

    • Author(s)
      高村浩由、和田寛子、呂楠、大野修、末永聖武、門田功
    • Organizer
      第55回天然有機化合物討論会
    • Place of Presentation
      同志社大学寒梅館
    • Related Report
      2013 Research-status Report
  • [Presentation] (-)-グンミフェロールの全合成・構造決定・構造活性相関2013

    • Author(s)
      高村浩由、和田寛子、呂楠、大野修、末永聖武、門田功
    • Organizer
      第104回有機合成シンポジウム
    • Place of Presentation
      早稲田大学国際会議場
    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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