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2011 Fiscal Year Final Research Report

Total Synthesis and Functional Analysis of Complex Natural Products

Research Project

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Project/Area Number 21241050
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section一般
Research Field Living organism molecular science
Research InstitutionTohoku University

Principal Investigator

SASAKI Makoto  東北大学, 大学院・生命科学研究科, 教授 (80235267)

Co-Investigator(Kenkyū-buntansha) FUWA Haruhiko  東北大学, 大学院・生命科学研究科, 准教授 (90359638)
KONOKI Keiichi  東北大学, 大学院・農学研究科, 准教授 (40292825)
Project Period (FY) 2009 – 2011
Keywords生物活性分子の設計・合成 / 天然物全合成
Research Abstract

Efficient synthetic routes to architecturally complex natural products with potent biological activities and molecular weights over 500 have been developed for exploring their biological functions. In particular, the first total synthesis and complete stereostructure determination of gambieric acid A have been accomplished. An efficient total synthesis of polycavernoside A has been also achieved in a convergent approach. In addition, efficient synthetic routes to the C1. C16 and C12. C36 fragments of goniodomin A have been developed by exploiting Stille-type coupling of thioesters.

  • Research Products

    (45 results)

All 2012 2011 2010 2009 Other

All Journal Article (14 results) (of which Peer Reviewed: 14 results) Presentation (25 results) Book (5 results) Remarks (1 results)

  • [Journal Article] Total synthesis of (-)-polycavernoside A : Suzuki. Miyaura coupling approach2012

    • Author(s)
      Yusuke Kasai, Takanori Ito, Makoto Sasaki
    • Journal Title

      Org. Lett.

      Volume: 14(in press)

    • Peer Reviewed
  • [Journal Article] Stereoselective synthesis of 2, 6-cis-substituted tetrahydropyrans : Bronsted acid-catalyzed intramolecular oxa-conjugate cyclization of2, 6-cis-unsaturated ester surrogates2012

    • Author(s)
      Haruhiko Fuwa, Naoki Ichinokawa, Kenkichi Noto, Makoto Sasaki
    • Journal Title

      J. Org. Chem.

      Volume: 77 Pages: 2558-2607

    • Peer Reviewed
  • [Journal Article] Recent applications of Suzuki. Miyaura cross-coupling to complex polycyclic ether synthesis2011

    • Author(s)
      Haruhiko Fuwa, Makoto Ebine, Makoto Sasaki
    • Journal Title

      J. Synth. Org. Chem. Jpn.(Special Issue in English)

      Volume: 69 Pages: 1251-1262

    • Peer Reviewed
  • [Journal Article] Studies toward the total synthesis of gambieric acids, potent antifungal polycyclic ethers : convergent synthesis of a fully elaborated2011

    • Author(s)
      Koichi Tsubone, Keisuke Hashizume, Haruhiko Fuwa, Makoto Sasaki
    • Journal Title

      GHIJ-ring fragment, Tetrahedron

      Volume: 67 Pages: 6600-6615

    • Peer Reviewed
  • [Journal Article] Biosynthesis-inspired intramolecular oxa-conjugate cyclization of α, β-unsaturated thioesters : Stereoselective synthesis of 2, 6-cis-substituted tetrahydropyrans2011

    • Author(s)
      Haruhiko Fuwa, Kenkichi Noto, Makoto Sasaki
    • Journal Title

      Org. Lett.

      Volume: 13 Pages: 1820-1823

    • Peer Reviewed
  • [Journal Article] A convergent synthesis of the C1. C16 segment of goniodomin A via palladium-catalyzed organostannane-thioester coupling2011

    • Author(s)
      Haruhiko Fuwa, Motohiro Nakajima, Jinglu Shi, Yoshiyuki Takeda, Tomoyuki Saito, Makoto Sasaki
    • Journal Title

      Org. Lett.

      Volume: 13 Pages: 1106-1109

    • Peer Reviewed
  • [Journal Article] Studies toward the total synthesis of gambieric acids : Convergent synthesis of the GHIJ-ring fragment having a side chain2011

    • Author(s)
      Koichi Tsubone, Keisuke Hashizume, Haruhiko Fuwa, Makoto Sasaki
    • Journal Title

      Tetrahedron Lett

      Volume: 51 Pages: 548-551

    • Peer Reviewed
  • [Journal Article] Synthetic studies on goniodomin A : Convergent synthesis of the C15. C36 segement via palladium-catalyzed organostannane-thioester coupling2011

    • Author(s)
      Tomoyuki Saito, Haruhiko Fuwa, Makoto Sasaki
    • Journal Title

      Tetrahedron

      Volume: 66 Pages: 429-445

    • Peer Reviewed
  • [Journal Article] Studies toward the total synthesis of gambieric acids : Stereocontrolled synthesis of a DEFG-ring model compound2010

    • Author(s)
      Haruhiko Fuwa, Sayaka Noji, Makoto Sasaki
    • Journal Title

      J. Org. Chem.

      Volume: 75 Pages: 5072-5082

    • Peer Reviewed
  • [Journal Article] Stereoselective synthesis of substituted tetrahydropyrans via domino olefin cross-metathesis/intramolecular oxa-conjugate cyclization2010

    • Author(s)
      Haruhiko Fuwa, Kenkichi Noto, Makoto Sasaki
    • Journal Title

      Org. Lett.

      Volume: 12 Pages: 1636-1639

    • Peer Reviewed
  • [Journal Article] Highly efficient synthesis of medium-sized lactones via oxidative lactonization : Concise total synthesis of isolaurepan2010

    • Author(s)
      Makoto Ebine, Yuto Suga, Haruhiko Fuwa, Makoto Sasaki
    • Journal Title

      Org. Biomol. Chem.

      Volume: 8 Pages: 39-42

    • Peer Reviewed
  • [Journal Article] Toward the total synthesis of goniodomin a, an actin-targeting marine polyether macrolide : convergent synthesis of the C15-C36 segment2009

    • Author(s)
      Tomoyuki Saito, Haruhiko Fuwa, Makoto Sasaki
    • Journal Title

      Org. Lett.

      Volume: 11 Pages: 5274-5277

    • Peer Reviewed
  • [Journal Article] Stereocontrolled synthesis of the DEFG-ring skeleton of gambieric acids2009

    • Author(s)
      Haruhiko Fuwa, Sayaka Noji, Makoto Sasaki
    • Journal Title

      Chem. Lett.

      Volume: 38 Pages: 866-867

    • Peer Reviewed
  • [Journal Article] Synthetic studies on gambieric acids, potent antifungal polycyclic ether natural products : Reassignment of the absolute configuration of the nonacyclic polyether core by NMR analysis of model compounds2009

    • Author(s)
      Haruhiko Fuwa, Kazuya Ishigai, Tomomi Goto, Akihiro Suzuki, Makoto Sasaki
    • Journal Title

      J. Org. Chem

      Volume: 74 Pages: 4024-4040

    • Peer Reviewed
  • [Presentation] 海産毒ポリカバノシドAの全合成研究2012

    • Author(s)
      葛西祐介、伊藤崇則、佐々木誠
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2012-03-27
  • [Presentation] ガンビエル酸Aの全合成研究2012

    • Author(s)
      石貝和也、橋詰圭佑、不破春彦、佐々木誠
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2012-03-27
  • [Presentation] ゴニオドミンAのC1. C16フラグメントの立体選択的合成2012

    • Author(s)
      中島基博、不破春彦、佐々木誠
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2012-03-27
  • [Presentation] ゴニオドミンAのC12. C36フラグメントの収束的合成2012

    • Author(s)
      松木田聖士、齋藤智之、不破春彦、佐々木誠
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2012-03-27
  • [Presentation] クロスカップリング反応を活用した天然物の全合成2011

    • Author(s)
      佐々木誠、鈴木宮浦
    • Organizer
      平成23年度有機合成化学前期講習会
    • Place of Presentation
      東京
    • Year and Date
      2011-06-22
  • [Presentation] 海産毒ポリカバノシドAの全合成研究2011

    • Author(s)
      葛西祐介、伊藤崇則、佐々木誠
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2011-03-28
  • [Presentation] ガンビエル酸類GHIJ環部フラグメント立体選択的合成とJ環側鎖導入法の開発2011

    • Author(s)
      局興一、橋詰圭祐、不破春彦、佐々木誠
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2011-03-28
  • [Presentation] ゴニオドミンAの全合成研究 : C1. C16セグメントの合成2011

    • Author(s)
      中島基博、師景、武田善行、齋藤智之、不破春彦、佐々木誠
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2011-03-28
  • [Presentation] ゴニオドミンAの全合成研究 : C26-C36セグメントの改良合成法の開発2011

    • Author(s)
      松木田聖士、不破春彦、佐々木誠
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2011-03-28
  • [Presentation] 複雑な海洋天然物の全合成(招待講演)2011

    • Author(s)
      佐々木誠
    • Organizer
      第13回生命化学研究会「分子で拓く生命化学」
    • Place of Presentation
      秋保
    • Year and Date
      2011-01-08
  • [Presentation] Synthetic studies on polycavernoside A2010

    • Author(s)
      Yusuke Kasai, Makoto Sasaki
    • Organizer
      The 2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2010-12-19
  • [Presentation] Studies toward the total synthesis of goniodomin A : Convergent synthesis of the C12. C36 fragment2010

    • Author(s)
      Tomoyuki Saito, Haruhiko Fuwa, Makoto Sasaki
    • Organizer
      The 2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2010-12-19
  • [Presentation] Convergent synthesis of the GHIJ-ring fragment of gambieric acids2010

    • Author(s)
      Koichi Tsubone, Keisuke Hashizume, Haruhiko Fuwa, Makoto Sasaki
    • Organizer
      The 2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2010-12-19
  • [Presentation] Convergent synthesis of the A/BCD-ring fragment of gambieric acid A2010

    • Author(s)
      Kazuya Ishigai, Haruhiko Fuwa, Makoto Sasaki
    • Organizer
      The 2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2010-12-19
  • [Presentation] ゴニオドミンAの全合成研究2010

    • Author(s)
      齋藤智之、不破春彦、佐々木誠
    • Organizer
      第98回有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2010-11-06
  • [Presentation] ガンビエル酸の全合成研究2010

    • Author(s)
      橋詰佳佑、局興一、石貝和也、不破春彦、佐々木誠
    • Organizer
      平成22年度化学系学協会東北大会
    • Place of Presentation
      盛岡
    • Year and Date
      2010-09-25
  • [Presentation] 環状エーテル構造を含む海洋天然物の全合成2010

    • Author(s)
      佐々木誠
    • Organizer
      第27回有機合成化学セミナー
    • Place of Presentation
      神戸
    • Year and Date
      2010-09-03
  • [Presentation] ポリカバノシドの全合成研究2010

    • Author(s)
      葛西祐介、佐々木誠
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      東大阪
    • Year and Date
      2010-03-28
  • [Presentation] ガンビエル酸AのA/BCD環部の合成研究2010

    • Author(s)
      石貝和也、不破春彦、佐々木誠
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      東大阪
    • Year and Date
      2010-03-28
  • [Presentation] ガンビエル酸類のGHIJ環部の合成研究2010

    • Author(s)
      局興一、橋詰圭祐、不破春彦、佐々木誠
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      東大阪
    • Year and Date
      2010-03-28
  • [Presentation] ゴニオドミンAのC15. C36セグメントの収束的合成2010

    • Author(s)
      齋藤智之、不破春彦、佐々木誠
    • Organizer
      第90回日本化学会春季年会
    • Place of Presentation
      東大阪
    • Year and Date
      2010-03-27
  • [Presentation] ガンビエル酸Aの全合成研究2009

    • Author(s)
      不破春彦、石貝和也、野地沙也加、局興一、橋詰佳祐、佐々木誠
    • Organizer
      第51回天然有機化合物討論会
    • Place of Presentation
      名古屋
    • Year and Date
      2009-10-07
  • [Presentation] ガンビエル酸DEFG環部の収束的合成2009

    • Author(s)
      野地沙也加、不破春彦、佐々木誠
    • Organizer
      平成21年度化学系学協会東北大会
    • Place of Presentation
      郡山
    • Year and Date
      2009-09-20
  • [Presentation] 酸化的ラクトン化による中員環ラクトン合成法の開発2009

    • Author(s)
      菅悠人、海老根真琴、不破春彦、佐々木誠
    • Organizer
      平成21年度化学系学協会東北大会
    • Place of Presentation
      郡山
    • Year and Date
      2009-09-20
  • [Presentation] 反応を活用した海洋天然物の全合成(招待講演)2009

    • Author(s)
      佐々木誠、鈴木宮浦
    • Organizer
      第19回万有福岡シンポジウム
    • Place of Presentation
      福岡
    • Year and Date
      2009-05-23
  • [Book] トップドラッグから学ぶ創薬化学2012

    • Author(s)
      佐々木誠
    • Total Pages
      158-159
    • Publisher
      東京化学同人
  • [Book] 天然物合成で活躍した反応実験のコツとポイント2011

    • Author(s)
      佐々木誠、不破春彦
    • Total Pages
      48-49
    • Publisher
      化学同人
  • [Book] ソレル有機化学(上/下)2009

    • Author(s)
      村田道雄、石橋正巳、木越英夫、佐々木誠
    • Total Pages
      854
    • Publisher
      東京化学同人
  • [Book] 巨大ポリエーテル天然物・ギムノシン-Aの全合成、天然物全合成の最新動向2009

    • Author(s)
      佐々木誠、塚野千尋
    • Total Pages
      228-243
    • Publisher
      シーエムシー出版
  • [Book] 天然物の全合成2000~2008(日本)2009

    • Author(s)
      佐々木誠
    • Total Pages
      85-88, 154-155
    • Publisher
      化学同人
  • [Remarks]

    • URL

      http://www.agri.tohoku.ac.jp/kanshoku/

URL: 

Published: 2013-07-31  

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