• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Synthetic studies on natural products containing highly substituted heterocyclic skeletons using ring-opening cyclization of spirocyclopropanes

Research Project

Project/Area Number 15K07853
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionUniversity of Toyama

Principal Investigator

NAMBU Hisanori  富山大学, 大学院医学薬学研究部(薬学), 准教授 (80399956)

Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2017: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords複素環天然物 / スピロシクロプロパン / 環化反応 / 多置換芳香族化合物 / 天然物 / 合成 / インドール / ベンゾフラン / 複素環化合物
Outline of Final Research Achievements

Ring-opening cyclization of spirocyclopropanes for the construction of a benzofuran skeleton was developed. The reaction of aryl-substituted spirocyclopropanes with acid catalysts proceeded smoothly to provide tetrahydrobenzofuran-4-ones in high yields. However, the reactions of non-substituted and electron-withdrawing group-substituted spirocyclopropanes using acid catalyst did not occur. After considerable experimentation, we found that iodide ion was an effective catalyst for these reactions.
We also developed the divergent synthesis of highly substituted indoles via the common synthetic intermediates tetrahydroindol-4-ones, which was prepared by the ring-opening cyclization of spirocyclopropanes with amines.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (26 results)

All 2018 2017 2016 2015 Other

All Journal Article (5 results) (of which Peer Reviewed: 5 results,  Open Access: 2 results,  Acknowledgement Compliant: 2 results) Presentation (20 results) (of which Int'l Joint Research: 5 results,  Invited: 2 results) Remarks (1 results)

  • [Journal Article] Novel Methods for the Synthesis of Heterocycles Using Highly Reactive Spirocyclopropanes2018

    • Author(s)
      南部 寿則
    • Journal Title

      YAKUGAKU ZASSHI

      Volume: 138 Issue: 1 Pages: 19-25

    • DOI

      10.1248/yakushi.17-00188

    • NAID

      130006300861

    • ISSN
      0031-6903, 1347-5231
    • Year and Date
      2018-01-01
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] An efficient route to highly substituted indoles via tetrahydroindol-4(5H)-one intermediates produced by ring-opening cyclization of spirocyclopropanes with amines2017

    • Author(s)
      Nambu H, Hirota W, Fukumoto M, Tamura T, Yakura T
    • Journal Title

      Chem Eur J

      Volume: 66 Issue: 66 Pages: 16799-16805

    • DOI

      10.1002/chem.201702622

    • NAID

      120006559814

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Acid-Catalyzed Ring-Opening Cyclization of Spirocyclopropanes for the Construction of a 2-Arylbenzofuran Skeleton: Total Synthesis of Cuspidan B2016

    • Author(s)
      Nambu, H.; Ono, N.; Yakura, T.
    • Journal Title

      Synthesis

      Volume: 48 Issue: 12 Pages: 1892-1901

    • DOI

      10.1055/s-0035-1561590

    • Related Report
      2016 Research-status Report 2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] An Efficient Method for the Synthesis of 2′,3′-Nonsubstituted Cycloalkane-1,3-dione-2-spirocyclopropanes Using (2-Bromoethyl)diphenylsulfonium Trifluoromethanesulfonate2016

    • Author(s)
      Nambu, H.; Ono, N.; Hirota, W.; Fukumoto, M.; Yakura, T.
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 64 Issue: 12 Pages: 1763-1768

    • DOI

      10.1248/cpb.c16-00625

    • NAID

      130005170648

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] An Efficient Synthesis of Cycloalkane-1,3-dione-2-spirocyclopropanes from 1,3-Cycloalkanediones Using (1-Aryl-2-bromoethyl)dimethylsulfonium Bromides: Application to a One-pot Synthesis of Tetrahydroindol-4(5H)-one2015

    • Author(s)
      Nambu, H.; Fukumoto, M.; Hirota, W.; Ono, N.; Yakura, T.
    • Journal Title

      Tetrahedron Lett.

      Volume: 56 Issue: 29 Pages: 4312-4315

    • DOI

      10.1016/j.tetlet.2015.05.069

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Presentation] ヨウ化物イオン触媒を用いるスピロシクロプロパンの位置選択的開裂―環化反応2018

    • Author(s)
      南部 寿則,大貫 悠太,小野 直樹,矢倉 隆之
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] スピロシクロプロパンの位置選択的開裂―環化反応による2位および3位置換テトラヒドロベンゾフラノンの選択的合成2018

    • Author(s)
      南部 寿則,大貫 悠太,小野 直樹,矢倉 隆之
    • Organizer
      第16回次世代を担う有機化学シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] Regioselective Ring-Opening Cyclization of Spirocyclopropanes with Amines: An Efficient Synthetic Method for Highly Substituted Indoles2017

    • Author(s)
      Hisanori Nambu, Masahiro Fukumoto, Wataru Hirota, Takafumi Tamura, Takayuki Yakura
    • Organizer
      The 26th International Society of Heterocyclic Chemistry Congress (26th ISHC Congress)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Acid-Catalyzed Ring-Opening Cyclization of Spirocyclopropanes: Total Synthesis of Benzofuran Natural Product Cuspidan B2017

    • Author(s)
      Hisanori Nambu, Yuta Onuki, Naoki Ono, Takayuki Yakura
    • Organizer
      The 26th International Society of Heterocyclic Chemistry Congress (26th ISHC Congress)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Concise Synthesis of Aspidospermidine Using Ring-Opening Cyclization of Spirocyclopropane with Amine2017

    • Author(s)
      Takafumi Tamura, Hisanori Nambu, Takayuki Yakura
    • Organizer
      The Second International Symposium on Toyama-Asia-Africa Pharmaceutical Network (2nd TAA-Pharm Symposium)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] スピロシクロプロパンを用いる多置換インドール合成法の開発とアスピドスペルマアルカロイドの合成研究2017

    • Author(s)
      南部 寿則,田村 貴史,廣田 渉,矢倉 隆之
    • Organizer
      第15回次世代を担う有機化学シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] スルホニウムイリドを用いるスピロシクロプロパンの開裂-環化反応によるクロマン骨格構築法の開発2017

    • Author(s)
      南部 寿則,大貫 悠太,矢倉 隆之
    • Organizer
      平成29年度有機合成化学北陸セミナー
    • Related Report
      2017 Annual Research Report
  • [Presentation] スピロシクロプロパンからのアスピドスペルミジンの短工程合成2017

    • Author(s)
      田村 貴史,南部 寿則,矢倉 隆之
    • Organizer
      日本薬学会北陸支部第129回例会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 環ひずみ解消を駆動力とする環化反応の開発と天然物合成への応用2016

    • Author(s)
      南部寿則
    • Organizer
      名城大学農学部天然物有機化学研究室特別講演会
    • Place of Presentation
      名古屋
    • Year and Date
      2016-12-20
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] スピロシクロプロパンの高反応性を活用する複素環化合物の新規合成法の開発2016

    • Author(s)
      南部寿則
    • Organizer
      日本薬学会北陸支部第128回例会(日本薬学会北陸支部奨励賞受賞講演)
    • Place of Presentation
      金沢
    • Year and Date
      2016-11-27
    • Related Report
      2016 Research-status Report
  • [Presentation] Efficient Method for the Synthesis of Highly Substituted Indoles and Benzofurans from Spirocyclopropanes2016

    • Author(s)
      Nambu, H.
    • Organizer
      Shandong University Special Lectures
    • Place of Presentation
      Jinan (China)
    • Year and Date
      2016-11-21
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] スピロシクロプロパンの開裂―環化つづく位置選択的アルキル化を経るアスピドスペルミジンの短工程合成2016

    • Author(s)
      南部寿則,田村貴史,矢倉隆之
    • Organizer
      平成28年度有機合成化学北陸セミナー
    • Place of Presentation
      金沢
    • Year and Date
      2016-10-07
    • Related Report
      2016 Research-status Report
  • [Presentation] 酸触媒を用いるスピロシクロプロパン開裂―環化反応の開発:ベンゾフラン天然物cuspidan B合成への応用2016

    • Author(s)
      南部寿則,小野直樹,矢倉隆之
    • Organizer
      第46回複素環化学討論会
    • Place of Presentation
      金沢
    • Year and Date
      2016-09-26
    • Related Report
      2016 Research-status Report
  • [Presentation] Acid-Catalyzed Ring-Opening Cyclization of Spirocyclopropanes for the Construction of Benofuran Skeleton2016

    • Author(s)
      Ono, N.; Nambu, H.; Yakura, T.
    • Organizer
      The First International Symposium on Toyama-Asia-Africa Pharmaceutical Network (1st TAA-Pharm Symposium)
    • Place of Presentation
      富山
    • Year and Date
      2016-09-12
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] 酸触媒スピロシクロプロパン開裂―環化反応を用いるベンゾフラン骨格構築法の開発:cuspidan B 合成への応用2016

    • Author(s)
      南部寿則,小野直樹,矢倉隆之
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(横浜市)
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] アミンによるスピロシクロプロパンの開裂―環化反応を用いるaspidospermidineの合成研究2016

    • Author(s)
      南部寿則,田村貴史,矢倉隆之
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(横浜市)
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] Ring-Opening Cyclization of Spirocyclopropanes with Amines: Rapid Access to 2-Substituted 4-Hydroxyindoles2015

    • Author(s)
      Nambu, H.; Fukumoto, M.; Hirota, W.; Yakura, T.
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015 (Pacifichem 2015)
    • Place of Presentation
      Hawaii Convention Center (Honolulu, Hawaii, USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] アミンを用いる位置選択的シクロプロパン開裂反応を鍵工程とする多置換インドール類の効率的合成法の開発2015

    • Author(s)
      廣田渉,福本昌紘,小野直樹,藤原朋也,南部寿則,矢倉隆之
    • Organizer
      日本薬学会北陸支部第127回例会
    • Place of Presentation
      富山大学杉谷キャンパス(富山市)
    • Year and Date
      2015-11-15
    • Related Report
      2015 Research-status Report
  • [Presentation] アミンによる位置選択的スピロシクロプロパンの開裂―環形成反応の開発と多置換インドール類の効率的合成2015

    • Author(s)
      南部寿則,福本昌紘,廣田渉,小野直樹,矢倉隆之
    • Organizer
      第41回反応と合成の進歩シンポジウム
    • Place of Presentation
      近畿大学(東大阪市)
    • Year and Date
      2015-10-26
    • Related Report
      2015 Research-status Report
  • [Presentation] スピロシクロプロパンの開裂―環化反応によるテトラヒドロベンゾフランの合成:cuspidan B 合成への応用2015

    • Author(s)
      小野直樹,南部寿則,矢倉隆之
    • Organizer
      平成27年度有機合成化学北陸セミナー
    • Place of Presentation
      富山観光ホテル(富山市)
    • Year and Date
      2015-10-02
    • Related Report
      2015 Research-status Report
  • [Remarks] 富山大学薬学部分子合成化学研究室ホームページ

    • URL

      http://www.pha.u-toyama.ac.jp/sboc/index-j.html

    • Related Report
      2017 Annual Research Report 2016 Research-status Report 2015 Research-status Report

URL: 

Published: 2015-04-16   Modified: 2019-03-29  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi