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Concise Total Synthesis of Polycyclic Bioactive Natural Products Based on New Integrated Reactions

Planned Research

Project AreaOrganic Synthesis based on Integration of Chemical Reactions. New Methodologies and New Materials
Project/Area Number 21106010
Research Category

Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Research InstitutionHokkaido University

Principal Investigator

TANINO Keiji  北海道大学, 理学(系)研究科(研究院), 教授 (40217146)

Project Period (FY) 2009-07-23 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥35,100,000 (Direct Cost: ¥27,000,000、Indirect Cost: ¥8,100,000)
Fiscal Year 2013: ¥6,890,000 (Direct Cost: ¥5,300,000、Indirect Cost: ¥1,590,000)
Fiscal Year 2012: ¥6,890,000 (Direct Cost: ¥5,300,000、Indirect Cost: ¥1,590,000)
Fiscal Year 2011: ¥6,890,000 (Direct Cost: ¥5,300,000、Indirect Cost: ¥1,590,000)
Fiscal Year 2010: ¥6,890,000 (Direct Cost: ¥5,300,000、Indirect Cost: ¥1,590,000)
Fiscal Year 2009: ¥7,540,000 (Direct Cost: ¥5,800,000、Indirect Cost: ¥1,740,000)
Keywords有機化学 / 集積合成手法 / 付加環化反応 / 生物活性物質 / 全合成 / 有機金属 / 中員環
Research Abstract

In connection with the research directed toward total synthesis of polycyclic natural products, we became intrigued with higher order cycloaddition approach for constructing medium-sized carbocycles. The use of a dicobalt acetylene complex possessing a leaving group and a nucleophile moiety was effective for achieving the [6+2], [6+4], and [5+2] cycloaddition reactions. These cascade reactions proceed through generation of a dicobalt hexacarbonyl propargyl cation, intermolecular addition (Nicholas reaction), followed by intramolecular cyclization. The results led us to explore applications of these new cycloaddition reactions in total synthesis of natural products containing seven, eight, nine, or ten-membered carbocycles.

Report

(6 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Annual Research Report
  • 2011 Annual Research Report
  • 2010 Annual Research Report
  • 2009 Annual Research Report
  • Research Products

    (41 results)

All 2014 2013 2012 2011 2010 2009 Other

All Journal Article (22 results) (of which Peer Reviewed: 22 results) Presentation (16 results) (of which Invited: 5 results) Book (2 results) Remarks (1 results)

  • [Journal Article] Synthetic studies on taxanes : construction of the tricyclic skeleton on the basis of the [6+2] cycloaddition reaction2014

    • Author(s)
      花田良輔, 三田地克彦, 谷野圭持
    • Journal Title

      Tetrahedron Letters

      Volume: 55 Issue: 5 Pages: 1097-1099

    • DOI

      10.1016/j.tetlet.2013.12.096

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Synthesis of the Right-hand Segment of Tubiferal A2014

    • Author(s)
      Takahiro Hiramatsu, Motomasa Takahashi, Keiji Tanino
    • Journal Title

      Tetrahedron Letters

      Volume: 55 Issue: 6 Pages: 1145-1147

    • DOI

      10.1016/j.tetlet.2013.12.069

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 1-Acetyl-2-silyoxycycloheptane Derivatives via Highly Stereoselective formal [5+2] Cycloaddition Reaction2014

    • Author(s)
      Mami Kudo, Fumikatsu Kondo, Hideki Maekawa, Tadashi Shimizu, Masaaki Miyashita, Keiji Tanino
    • Journal Title

      Tetrahedron Letters

      Volume: 55 Issue: 6 Pages: 1192-1195

    • DOI

      10.1016/j.tetlet.2013.12.102

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 2-Cyano-1,4-cycloheptadiene Derivatives via Divinylcyclopropane Rearrangement and Alkylation of Novel Cycloheptadienyl Anion Species2013

    • Author(s)
      Takumasa Yamada, Fumihiko Yoshimura, Keiji Tanino
    • Journal Title

      Tetrahedron Letters

      Volume: 54 Issue: 6 Pages: 522-525

    • DOI

      10.1016/j.tetlet.2012.11.070

    • Related Report
      2013 Annual Research Report 2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Transformations of 1-(Oxiranylmethyl)-1,2,3-triazoles into 2-(Oxiranylmethyl)-1,2,3-triazoles and Alkanenitriles2013

    • Author(s)
      Kosuke Namba, Ayumi Osawa, Akane Mera, Keiji Tanino
    • Journal Title

      Synlett

      Volume: 24 Issue: 02 Pages: 207-210

    • DOI

      10.1055/s-0032-1317937

    • NAID

      120005358931

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Tetrasubstituted Pyrrolidine Derivatives Employing β-Lactam as a Chiral Building Block2013

    • Author(s)
      Genta Tadano, Koji Ishikura, Keiji Tanino
    • Journal Title

      Heterocycles

      Volume: 87 Issue: 11 Pages: 2267-2281

    • DOI

      10.3987/com-13-12812

    • NAID

      40019844682

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Zoanthamine Alkaloids2012

    • Author(s)
      F. Yoshimura, K. Tanino, and M. Miyashita
    • Journal Title

      Acc. Chem. Res

      Volume: 45 (5) Issue: 5 Pages: 746-755

    • DOI

      10.1021/ar200267a

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] A small molecule inhibitor of p53-inducible protein phosphatase PPM1D2012

    • Author(s)
      八木寛陽
    • Journal Title

      Bioorganic & Medicinal Chemistry Letters

      Volume: VOL.22 Issue: 1 Pages: 729-732

    • DOI

      10.1016/j.bmcl.2011.10.084

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Intramolecular Conjugate Addition ofα,β-Unsaturated Lactones Having an Alkanenitrile Side Chain : Stereocontrolled Construction of Carbocycles with Quaternary Carbon Atoms2012

    • Author(s)
      Yoshimura, F.; Torizuka, M.; Mori, G.; Tanino, K.
    • Journal Title

      Synlett

      Volume: 23巻 Issue: 02 Pages: 251-254

    • DOI

      10.1055/s-0031-1290074

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hg(OTf)2-Catalyzed Vinylogous Semi-Pinacol Rearrangement Leading to 1,4-Dihydroquinolines2012

    • Author(s)
      Kosuke Namba
    • Journal Title

      Organic Letters

      Volume: 14 Issue: 5 Pages: 1222-1225

    • DOI

      10.1021/ol2034492

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled synthesis of Carbocyclic Compounds with a Quaternary Carbon Atom based on SN2' Alkylation of γ,δ-Epoxy-α,β-unsaturated Ketones2012

    • Author(s)
      谷野圭持、吉村文彦, ほか1名
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 10 Issue: 28 Pages: 5431-5442

    • DOI

      10.1039/c2ob25719j

    • NAID

      120005228736

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Concese [4+3]Cycloadditions of Pyrroles Leading to Tropinone Derivatives2012

    • Author(s)
      Fuchigami, R. ; Namba, K. ; Tanino, K.
    • Journal Title

      Tetrahedron Letter

      Volume: 53 Issue: 43 Pages: 5725-5728

    • DOI

      10.1016/j.tetlet.2012.07.130

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] One-Pot Synthesis of Highly Fluorescent 2,5-Disubstituted-1,3a,6a-triazapentalene2012

    • Author(s)
      K. Namba, A. Mera, A. Osawa, E. Sakuda, N. Kitamura and K. Tanino
    • Journal Title

      Org. Lett.

      Volume: 14 Issue: 21 Pages: 5554-5557

    • DOI

      10.1021/ol302668y

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct Synthesis of Fluorescent 1,3a,6a-Triazapentalene Derivatives via Click-Cyclization- Aromatization Cascade Reaction2011

    • Author(s)
      K. Namba, A. Osawa, S. Ishizaka, N. Kitamura, and K. Tanino
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133, (8) Issue: 30 Pages: 11466-11469

    • DOI

      10.1021/ja203917r

    • Related Report
      2013 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Solanoeclepin A2011

    • Author(s)
      K. Tanino, M. Takahashi, Y. Tomata, H. Tokura, T. Uehara, T. Narabu, and M. Miyashita
    • Journal Title

      Nature Chem

      Volume: 3, (6) Issue: 6 Pages: 484-488

    • DOI

      10.1038/nchem.1044

    • Related Report
      2013 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Formal [6+4] Cycloaddition of a Dicobalt Acetylene Complex with Furan Derivatives2011

    • Author(s)
      K. Dota, T. Shimizu, S. Hasegawa, M. Miyashita, and K. Tanino
    • Journal Title

      Tetrahedron Lett

      Volume: 52, (8) Issue: 8 Pages: 910-912

    • DOI

      10.1016/j.tetlet.2010.12.063

    • Related Report
      2013 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthetic Studies of the Zoanthamine Alkaloids : Total Synthesis of Zoanthenol Based on Isoaromatization Strategy2011

    • Author(s)
      谷野圭持、宮下正昭, ほか2名
    • Journal Title

      Chemistry an Asian Journal

      Volume: 6 Issue: 3 Pages: 922-931

    • DOI

      10.1002/asia.201000552

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Formal [6+4] Cycloaddition of a Dicobalt Acetylene Complex with Furan Derivatives2011

    • Author(s)
      宮下正昭、谷野圭持, ほか3名
    • Journal Title

      Tetrahedron Letters

      Volume: Vol.52 Pages: 910-912

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Furanether B.Construction of a Hydroazulene Skeleton via a Novel [5+2] Cycloaddition Reaction of Silyloxyallene2010

    • Author(s)
      宮下正昭、谷野圭持, ほか4名
    • Journal Title

      Chemistry Letters

      Volume: Vol.39 Pages: 630-632

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cyclooctanone Synthesis via a Formal [6+2] Cycloaddition Reaction of a Dicobalt Acetylene Complex2010

    • Author(s)
      宮下正昭、谷野圭持, ほか2名
    • Journal Title

      Tetrahedron Letters

      Volume: Vol.51 Pages: 3983-3986

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Zoanthenol2009

    • Author(s)
      宮下正昭、谷野圭持, ほか2名
    • Journal Title

      Angew.Chem.Int.Ed. Vol.48

      Pages: 8905-8908

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthetic Studies of the Zoanthamine Alkaloids : The Total Syntheses of Norzoanthamine and Zoanthamine2009

    • Author(s)
      宮下正昭、谷野圭持, ほか5名
    • Journal Title

      Chem.Eur.J. Vol.15

      Pages: 6626-6644

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] 新しい高次付加環化反応を基盤とする天然物合成2013

    • Author(s)
      谷野圭持
    • Organizer
      理研セミナー「未来に繋ぐ天然物合成化学」
    • Place of Presentation
      豊中
    • Year and Date
      2013-05-13
    • Related Report
      2013 Final Research Report
  • [Presentation] 新しい縮環骨格構築法を基盤とする高次構造天然物の全合成2013

    • Author(s)
      谷野圭持
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津
    • Related Report
      2013 Final Research Report
  • [Presentation] 社会に役立つ有機合成を求めて:シストセンチュウふ化促進物質の全合成2013

    • Author(s)
      谷野圭持
    • Organizer
      平成24年度関学化学フォーラム「有機合成化学を究める」
    • Place of Presentation
      関西学院大学(三田)
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] 新しい縮環骨格構築法を基盤とする高次構造天然物の全合成2013

    • Author(s)
      谷野圭持
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学(草津市)
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Asymmetric Total Synthesis of Solanoeclepin A2012

    • Author(s)
      谷野圭持
    • Organizer
      The 5th GCOE International Symposium : Catalysis as the Basis for the Innovation in Materials Science
    • Place of Presentation
      北海道大学(札幌市)(招待講演)
    • Year and Date
      2012-02-21
    • Related Report
      2011 Annual Research Report
  • [Presentation] 社会に役立つ「ものづくり」としての多段階合成を求めて:シストセンチュウふ化促進物質の全合成2012

    • Author(s)
      谷野圭持
    • Organizer
      有機合成化学を起点とするものづくり戦略 第2回ミニシンポジウム
    • Place of Presentation
      北海道大学(札幌市)
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Design, Tactics, and Findings in Natural Product Synthesis2011

    • Author(s)
      K. Tanino
    • Organizer
      The Nagoya Medal of Organic Chemistry 2011
    • Place of Presentation
      Nagoya
    • Year and Date
      2011-11-14
    • Related Report
      2013 Final Research Report
  • [Presentation] Design, Tactics, and Findings in Natural Product Synthesis2011

    • Author(s)
      谷野圭持
    • Organizer
      The Nagoya Medal of Organic Chemistry 2011
    • Place of Presentation
      名古屋大学(名古屋市)(招待講演)
    • Year and Date
      2011-11-14
    • Related Report
      2011 Annual Research Report
  • [Presentation] Total Synthesis of Solanoeclepin A2011

    • Author(s)
      K. Tanino
    • Organizer
      22nd French-Japanese Symposium of Medicinal and Fine Chemistry
    • Place of Presentation
      Rouen
    • Year and Date
      2011-09-14
    • Related Report
      2013 Final Research Report
  • [Presentation] Total Synthesis of Solanoeclepin A2011

    • Author(s)
      谷野圭持
    • Organizer
      22nd French-Japanese Symposium of Medicinal and Fine Chemistry
    • Place of Presentation
      the Chambre de Commerce etd・Industrie(フランス)(招待講演)
    • Year and Date
      2011-09-14
    • Related Report
      2011 Annual Research Report
  • [Presentation] シストセンチュウ孵化促進物質の不斉全合成2011

    • Author(s)
      谷野圭持
    • Organizer
      第28回有機合成化学セミナー
    • Place of Presentation
      ホテル滝の湯(天童市)(招待講演)
    • Year and Date
      2011-09-02
    • Related Report
      2011 Annual Research Report
  • [Presentation] Asymmetric Total Synthesis of Solanoeclepin A2011

    • Author(s)
      K. Tanino
    • Organizer
      NTU-JSPS Joint Symposium "Recent Advances in Organic Syntheses
    • Place of Presentation
      Singapore
    • Year and Date
      2011-08-01
    • Related Report
      2013 Final Research Report
  • [Presentation] Asymmetric Total Synthesis of Solanoeclepin A2011

    • Author(s)
      谷野圭持
    • Organizer
      NTU-JSPS Joint Symposium "Recent Advances in Organic Syntheses"
    • Place of Presentation
      南洋理工大学(シンガポール)(招待講演)
    • Year and Date
      2011-08-01
    • Related Report
      2011 Annual Research Report
  • [Presentation] 新しい高次付加環化反応に基づくテルペノイドの全合成2009

    • Author(s)
      谷野圭持
    • Organizer
      平成21年度後期(秋季)有機合成化学講習会
    • Place of Presentation
      日本薬学会長井記念ホール(東京都)
    • Year and Date
      2009-11-19
    • Related Report
      2009 Annual Research Report
  • [Presentation] 新しい高次付加環化反応を基盤とする天然物合成

    • Author(s)
      谷野 圭持
    • Organizer
      理研セミナー「未来に繋ぐ天然物合成化学」
    • Place of Presentation
      大阪大学(豊中市)
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] シストセンチュウ孵化促進物質の不斉全合成

    • Author(s)
      谷野 圭持
    • Organizer
      新学術領域研究「生合成マシナリー:生物活性物質構造多様性創出システムの解明と制御」第5回公開シンポジウム
    • Place of Presentation
      北海道大学(札幌市)
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Book] ゾアンタミン系アルカロイドの全合成, 天然物全合成の最新動向; 北泰行 監修2009

    • Author(s)
      宮下正昭; 谷野圭持; 吉村文彦
    • Publisher
      シーエムシー出版,東京
    • Related Report
      2013 Final Research Report
  • [Book] 天然物全合成の最新動向2009

    • Author(s)
      宮下正昭、谷野圭持、吉村文彦
    • Total Pages
      22
    • Publisher
      シーエムシー出版
    • Related Report
      2009 Annual Research Report
  • [Remarks]

    • URL

      http://barato.sci.hokudai.ac.jp/~oc2/

    • Related Report
      2013 Final Research Report

URL: 

Published: 2009-04-01   Modified: 2018-03-28  

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