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Efficient Synthesis of Marine Polycyclic Ethers

Research Project

Project/Area Number 19350023
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionOkayama University

Principal Investigator

KADOTA Isao  Okayama University, 大学院・自然科学研究科, 教授 (30250666)

Co-Investigator(Kenkyū-buntansha) TAKAMURA Hiroyoshi  岡山大学, 大学院・自然科学研究科, 助教 (70422798)
Project Period (FY) 2007 – 2009
Project Status Completed (Fiscal Year 2009)
Budget Amount *help
¥19,110,000 (Direct Cost: ¥14,700,000、Indirect Cost: ¥4,410,000)
Fiscal Year 2009: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2008: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2007: ¥9,490,000 (Direct Cost: ¥7,300,000、Indirect Cost: ¥2,190,000)
Keywords合成有機化学 / 天然有機化合物 / 海洋産天然物 / ポリ環状エーテル / 収束的合成 / 分子内アリル化 / 閉環メタセシス / 全合成 / ブレベナール / シガトキシン / 海産天然物 / 収束適合性
Research Abstract

In recent years there has been an explosion of interest in biologically active natural products of marine origin. Due to their structural novelty and toxicity, polycyclic ethers isolated from marine algae are particularly attractive targets for synthetic chemists. Since further biological studies are hampered by the limited availability from nature, chemical synthesis has been the sole realistic way to obtain sufficient amounts of the polycyclic ethers. In this study, convergent synthesis of brevenal and ciguatoxin CTX3C via the intramolecular allyaltion followed by ring-closing metathesis were examined.

Report

(4 results)
  • 2009 Annual Research Report   Final Research Report ( PDF )
  • 2008 Annual Research Report
  • 2007 Annual Research Report
  • Research Products

    (55 results)

All 2010 2009 2008 2007 Other

All Journal Article (25 results) (of which Peer Reviewed: 13 results) Presentation (29 results) Remarks (1 results)

  • [Journal Article] Stereoselective synthesis of the C14-C24 degraded fragment of symbiodinolide.2010

    • Author(s)
      Takamura, H., Kadonaga, Y., Kadota, I., Uemura, D.
    • Journal Title

      Tetrahedron Lett. 51,(19)

      Pages: 2603-2605

    • Related Report
      2009 Final Research Report
  • [Journal Article] Convergent synthesis of the A-E ring segment of ciguatoxin CTX3C.2009

    • Author(s)
      Kadota, I., Abe, T., Uni, M., Takamura, H., Yamamoto, Y.
    • Journal Title

      Tetrahedron 65,(37)

      Pages: 7784-7789

    • Related Report
      2009 Final Research Report
  • [Journal Article] Stereoselective synthesis and absolute configuration of the C33-C42 fragment of symbiodinolide.2009

    • Author(s)
      Takamura, H., Kadonaga, Y., Yamano, Y., Han, C., Kadota, I., Uemura, D.
    • Journal Title

      Tetrahedron 65,(36)

      Pages: 7449-7456

    • Related Report
      2009 Final Research Report
  • [Journal Article] Stereoselective Synthesis and Absolute Configuration of the C1'-C25' Fragment of Symbiodinolide.2009

    • Author(s)
      Takamura, H., Murata, T., Asai, T., Kadota, I., Uemura, D.
    • Journal Title

      J. Org. Chem. 74,(17)

      Pages: 6658-6666

    • Related Report
      2009 Final Research Report
  • [Journal Article] Selective cleavage of primary MPM ethers with TMSI/Et3N.2009

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

      Tetrahedron Lett. 50,(31)

      Pages: 4552-4553

    • Related Report
      2009 Final Research Report
  • [Journal Article] Synthesis and Structural Revision of Symbiodinolide C23-C34 Fragment.2009

    • Author(s)
      Murata, T., Sano, M., Takamura, H., Kadota, I., Uemura, D.
    • Journal Title

      J. Org. Chem. 74,(13)

      Pages: 4797-4803

    • Related Report
      2009 Final Research Report
  • [Journal Article] Total Synthesis of Brevenal.2009

    • Author(s)
      Takamura, H., Kikuchi, S., Nakamura, Y., Yamagami, Y., Kishi, T., Kadota, I., Yamamoto, Y.
    • Journal Title

      Org. Lett. 11,(12)

      Pages: 2531-2534

    • NAID

      110009757645

    • Related Report
      2009 Final Research Report
  • [Journal Article] A transannular Diels-Alder strategy for the construction of the CDE ring system of nakiterpiosin.2009

    • Author(s)
      Takamura, H., Yamagami, Y., Ito, T., Ito, M., Arimoto, H., Kadota, I., Uemura, D.
    • Journal Title

      Heterocycles 77,(1)

      Pages: 351-364

    • Related Report
      2009 Final Research Report
  • [Journal Article] Synthesis and structural determination of the C33-C42 fragment of symbiodinolide.2009

    • Author(s)
      Takamura, H., Kadonaga, Y., Yamano, Y., Han, C., Aoyama, Y., Kadota, I., Uemura, D.
    • Journal Title

      Tetrahedron Lett. 50,(8)

      Pages: 863-866

    • Related Report
      2009 Final Research Report
  • [Journal Article] Convergent synthesis of the A-E ring segment of ciguatoxin CTX3C2009

    • Author(s)
      Isao Kadota
    • Journal Title

      Tetrahedron 65

      Pages: 7784-7789

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective synthesis and absolute configuration of the C33-C42 fragment of symbiodinolide2009

    • Author(s)
      Hiroyoshi Takamura
    • Journal Title

      Tetrahedron 65

      Pages: 7449-7456

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Synthesis and Absolute Configuration of the C1'-C25' Fragment of Symbiodinolide2009

    • Author(s)
      Hiroyoshi Takamura
    • Journal Title

      Journal of Organic Chemistry 74

      Pages: 6658-6666

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Selective cleavage of primary MPM ethers with TMSI/Et3N2009

    • Author(s)
      Isao Kadota
    • Journal Title

      Tetrahedron Letters 50

      Pages: 4552-4553

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Brevenal2009

    • Author(s)
      Hiroyoshi Takamura
    • Journal Title

      Organic Letters 11

      Pages: 2531-2534

    • NAID

      110009757645

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A transannular Diels-Alder strategy for the construction of the CDE ring system of nakiterpiosin2009

    • Author(s)
      Hiroyoshi Takamura
    • Journal Title

      Heterocycles 77

      Pages: 351-364

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and structural determination of the C33-C42 fragment of symbiodinolide2009

    • Author(s)
      Hiroyoshi Takamura
    • Journal Title

      Tetrahedron Letters 50

      Pages: 863-866

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled synthesis of the C79-C96 fragment of symbiodinolide.2008

    • Author(s)
      Takamura, H., Ando, J., Abe, T., Murata, T., Kadota, I., Uemura, D.
    • Journal Title

      Tetrahedron Lett. 49,(31)

      Pages: 4626-4629

    • Related Report
      2009 Final Research Report
  • [Journal Article] A cross-metathesis approach to the stereocontrolled synthesis of the AB ring segment of ciguatoxin.2008

    • Author(s)
      Kadota, I., Abe, T., Uni, M., Takamura, H., Yamamoto, Y.
    • Journal Title

      Tetrahedron Lett. 49,(22)

      Pages: 3643-3647

    • NAID

      120002306949

    • Related Report
      2009 Final Research Report
  • [Journal Article] A Cross-metathesis Approach to the Stereocontrolled Synthesis of the AB Ring Segment of Ciguatoxin2008

    • Author(s)
      I. Kadota
    • Journal Title

      Tetrahedron Letters 49

      Pages: 3643-3647

    • NAID

      120002306949

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled Synthesis of the C79-C96 Fragment of Symbiodinolide2008

    • Author(s)
      H. Takamura
    • Journal Title

      Tetrahedron Letters 49

      Pages: 4626-4629

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Solvent-Controlled Stereoselective Formation of a Cyclic Ether in the Lewis Acid-Mediated Allylation of anα-Chloroacetoxy Acyclic Ether. Very High Stereoselectivity in CH3CN vs Low Stereoselectivity in CH2Cl2.2007

    • Author(s)
      Gridnev, I.D., Kikuchi, S., Touchy, A.S., Kadota, I., Yamamoto, Y.
    • Journal Title

      J. Org. Chem. 72,(22)

      Pages: 8371-8375

    • Related Report
      2009 Final Research Report
  • [Journal Article] A Convergent Approach to the Formal Total Synthesis of Hemibrevetoxin B2007

    • Author(s)
      I. Kadota
    • Journal Title

      Tetrahedron Letters 48

      Pages: 219-221

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] ブレベトキシンBの全合成2007

    • Author(s)
      門田 功
    • Journal Title

      有機合成化学協会誌 65

      Pages: 430-438

    • NAID

      10020137685

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Solvent-Controlled Stereoselective Formation of a Cyclic Ether in the Lewis Acid-Mediated Allylation of an α-Chloroacetoxy Acyclic Ether. Very High Stereoselectivity in CH_3CN vs Low Stereoselectivity in CH_2Cl_22007

    • Author(s)
      I.D. Gridnev
    • Journal Title

      The Journal of Organic Chemistry 71

      Pages: 8371-8375

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Formal Total Synthesis of Hemibrevetoxin B via the Intramolecular Allylation Followed by Ring-closing Metathesis2007

    • Author(s)
      I. Kadota
    • Journal Title

      Heterocycles 74

      Pages: 617-627

    • NAID

      40015919615

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Presentation] シンビオジノライドC14-C24フラグメントの立体選択的合成2010

    • Author(s)
      角永悠一郎
    • Organizer
      日本化学会第90春期年会
    • Place of Presentation
      近畿大学本部キャンパス(大阪府)
    • Year and Date
      2010-03-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] シンビオジノライドC94-C104フラグメントの合成研究2010

    • Author(s)
      津田浩輔
    • Organizer
      日本化学会第90春期年会
    • Place of Presentation
      近畿大学本部キャンパス(大阪府)
    • Year and Date
      2010-03-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] 縮環エーテル類に対する新規核間メチル基導入法2010

    • Author(s)
      岸敬之
    • Organizer
      日本化学会第90春期年会
    • Place of Presentation
      近畿大学本部キャンパス(大阪府)
    • Year and Date
      2010-03-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] ピラニシンの全合成2010

    • Author(s)
      山神雄司
    • Organizer
      日本化学会第90春期年会
    • Place of Presentation
      近畿大学本部キャンパス(大阪府)
    • Year and Date
      2010-03-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] シガトキシンCTX3CのHIJKLM環部の合成研究2010

    • Author(s)
      阿部享史
    • Organizer
      日本化学会第90春期年会
    • Place of Presentation
      大阪
    • Year and Date
      2010-03-28
    • Related Report
      2009 Final Research Report
  • [Presentation] シガトキシンCTX3CのEFGH環部の合成研究2010

    • Author(s)
      藤田直弥
    • Organizer
      日本化学会第90春期年会
    • Place of Presentation
      大阪
    • Year and Date
      2010-03-28
    • Related Report
      2009 Final Research Report
  • [Presentation] シガトキシンCTX3CのHIJKLM環部の合成研究2010

    • Author(s)
      阿部享史
    • Organizer
      日本化学会第90春期年会
    • Place of Presentation
      近畿大学本部キャンパス(大阪府)
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] シガトキシンCTX3CのE環部の合成2010

    • Author(s)
      佐藤優樹
    • Organizer
      日本化学会第90春期年会
    • Place of Presentation
      近畿大学本部キャンパス(大阪府)
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] シガトキシンCTX3CのEFGH環部の合成研究2010

    • Author(s)
      藤田直弥
    • Organizer
      日本化学会第90春期年会
    • Place of Presentation
      近畿大学本部キャンパス(大阪府)
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] Total Synthesis of Brevenal2009

    • Author(s)
      Isao Kadota
    • Organizer
      The 11th International Kyoto Conference on New Aspects of Organic Chemistry(IKCOC-11)
    • Place of Presentation
      リーグロイヤルホテル京都(京都府)
    • Year and Date
      2009-11-11
    • Related Report
      2009 Annual Research Report
  • [Presentation] 海洋産天然物ブレベナールの全合成2009

    • Author(s)
      門田功
    • Organizer
      2009年日本化学会西日本大会
    • Place of Presentation
      松山
    • Year and Date
      2009-11-07
    • Related Report
      2009 Final Research Report
  • [Presentation] 海洋産天然物ブレベナールの全合成(招待講演)2009

    • Author(s)
      門田功
    • Organizer
      2009年日本化学会西日本大会
    • Place of Presentation
      愛媛大学城北キャンパス(愛媛県)
    • Year and Date
      2009-11-07
    • Related Report
      2009 Annual Research Report
  • [Presentation] シンビオジノライドC14-C24およびC33-C42フラグメントの立体選択的合成2009

    • Author(s)
      角永悠一郎
    • Organizer
      2009年日本化学会西日本大会
    • Place of Presentation
      愛媛大学城北キャンパス(愛媛県)
    • Year and Date
      2009-11-07
    • Related Report
      2009 Annual Research Report
  • [Presentation] ブレベナールの全合成2009

    • Author(s)
      山神雄司
    • Organizer
      第51回天然有機化合物討論会
    • Place of Presentation
      名古屋
    • Year and Date
      2009-10-09
    • Related Report
      2009 Final Research Report
  • [Presentation] ブレベナールの全合成2009

    • Author(s)
      山神雄司
    • Organizer
      第51回天然有機化合物討論会
    • Place of Presentation
      名古屋市公会堂(愛知県)
    • Year and Date
      2009-10-09
    • Related Report
      2009 Annual Research Report
  • [Presentation] ブレベナールの全合成2009

    • Author(s)
      山神雄司
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2009-03-29
    • Related Report
      2009 Final Research Report 2008 Annual Research Report
  • [Presentation] シガトキシンCTX3CのEFGH環部の合成研究2009

    • Author(s)
      佐藤優樹
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2009-03-29
    • Related Report
      2008 Annual Research Report
  • [Presentation] シンビオジノライドC23-C34フラグメントの合成2009

    • Author(s)
      佐野将之
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2009-03-28
    • Related Report
      2008 Annual Research Report
  • [Presentation] シンビオジノライドC33-C42フラグメントの合成および構造決定2009

    • Author(s)
      角永悠一郎
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2009-03-28
    • Related Report
      2008 Annual Research Report
  • [Presentation] シンビオジノライドC79-C96フラグメントの立体選択的合成2009

    • Author(s)
      阿部享史
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2009-03-28
    • Related Report
      2008 Annual Research Report
  • [Presentation] 超炭素鎖有機分子シンビオジノライドの合成研究2008

    • Author(s)
      高村浩由
    • Organizer
      日本化学会西日本大会
    • Place of Presentation
      長崎
    • Year and Date
      2008-11-15
    • Related Report
      2008 Annual Research Report
  • [Presentation] 海洋産ポリ環状エーテルの合成戦略2008

    • Author(s)
      門田功
    • Organizer
      第24回若手化学者のための化学道場
    • Place of Presentation
      徳島
    • Year and Date
      2008-09-11
    • Related Report
      2009 Final Research Report
  • [Presentation] Convergent Synthesis of Marine Polycyclic Ethers2008

    • Author(s)
      門田功
    • Organizer
      5th International Symposium on Integrated Synthesis
    • Place of Presentation
      神戸
    • Year and Date
      2008-09-05
    • Related Report
      2009 Final Research Report
  • [Presentation] シガトキシンCTX3CのA-E環部の合成研究2008

    • Author(s)
      阿部享史
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      東京
    • Year and Date
      2008-03-28
    • Related Report
      2009 Final Research Report
  • [Presentation] ブレベナールの合成研究2008

    • Author(s)
      菊池重俊
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大学池袋キャンパス
    • Year and Date
      2008-03-27
    • Related Report
      2007 Annual Research Report
  • [Presentation] シガトキシンAB環部の立体選択的合成2008

    • Author(s)
      阿部享史
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大学池袋キャンパス
    • Year and Date
      2008-03-27
    • Related Report
      2007 Annual Research Report
  • [Presentation] シガトキシンCTX3CのA-E環部の合成研究2008

    • Author(s)
      宇仁巳由紀
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大学池袋キャンパス
    • Year and Date
      2008-03-27
    • Related Report
      2007 Annual Research Report
  • [Presentation] シンビオジノライドの合成研究(1)2008

    • Author(s)
      村田健史
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大学池袋キャンパス
    • Year and Date
      2008-03-27
    • Related Report
      2007 Annual Research Report
  • [Presentation] シンビオジノライドの合成研究(2)2008

    • Author(s)
      佐野将之
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大学池袋キャンパス
    • Year and Date
      2008-03-27
    • Related Report
      2007 Annual Research Report
  • [Remarks]

    • URL

      http://chem.okayama-u.ac.jp/~organic/homejpn.html

    • Related Report
      2009 Final Research Report

URL: 

Published: 2007-04-01   Modified: 2016-04-21  

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