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

Natural Product Synthesis by Utilizing Small Ring Hydrocarbons Possessing Hetero Substituents

Research Project

Project/Area Number 15H03806
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionHokkaido University

Principal Investigator

Tanino Keiji  北海道大学, 理学研究院, 教授 (40217146)

Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥16,640,000 (Direct Cost: ¥12,800,000、Indirect Cost: ¥3,840,000)
Fiscal Year 2017: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2016: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2015: ¥5,980,000 (Direct Cost: ¥4,600,000、Indirect Cost: ¥1,380,000)
Keywords小員環 / 開環反応 / 環化反応 / 酸素求核剤 / 合成化学 / 置換反応 / アルキルハライド / アルコール / 有機化学 / 天然物 / 転位反応
Outline of Final Research Achievements

New synthetic reactions utilizing small ring hydrocarbons with hetero substituents were developed. A bicyclo[4.2.0]octane derivative was synthesized on the basis of the intramolecular cyclization reaction of a vinyl sulfide possessing a leaving group. A new divinylcyclobutane rearrangement reaction was developed by using 2,2-divinylcyclobutanecarbonitrile as a useful building block. The adduct derived from the four-membered nitrile and a cyclohexanone derivative was treated with an acid, giving rise to a bicyclo[6.4.0]undecane derivative via the Cope rearrangement.
On the other hand, squarate dianion was found to exhibit high reactivity as an oxygen nucleophile, which enabled the transformation of primary and secondary chlorides and bromides to the corresponding alcohols in high yields.

Report

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

    (24 results)

All 2018 2017 2016 2015

All Journal Article (12 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 12 results,  Acknowledgement Compliant: 7 results,  Open Access: 3 results) Presentation (12 results) (of which Int'l Joint Research: 5 results,  Invited: 12 results)

  • [Journal Article] Enantioselective Total Synthesis of (+)-Iso-A82775C, a Proposed Biosynthetic Precursor of Chloropupukeananin2017

    • Author(s)
      Suzuki Takahiro、Watanabe Soichiro、Kobayashi Susumu、Tanino Keiji
    • Journal Title

      Organic Letters

      Volume: 19 Issue: 4 Pages: 922-925

    • DOI

      10.1021/acs.orglett.7b00085

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nucleophilic Addition of Alkanenitriles to Aldehydes via N-Silyl Ketene Imines Generated In Situ2017

    • Author(s)
      Yoshimura Fumihiko、Tanino Keiji、Saito Hiroki、Abe Taiki
    • Journal Title

      Synlett

      Volume: 28 Issue: 14 Pages: 1816-1820

    • DOI

      10.1055/s-0036-1588424

    • NAID

      120006502485

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Inhibition of Ser/Thr phosphatase PPM1D induces neutrophil differentiation in HL-60 cells2017

    • Author(s)
      Kamada Rui、Kudoh Fuki、Yoshimura Fumihiko、Tanino Keiji、Sakaguchi Kazuyasu
    • Journal Title

      The Journal of Biochemistry

      Volume: 162 Pages: 303-308

    • DOI

      10.1093/jb/mvx032

    • NAID

      40021380581

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Construction of Bicyclic Systems Containing an Oxygen Bridge by Isomerization of Cyclic Epoxy Alcohols2017

    • Author(s)
      Masaru Iwakura, Hiroshi Tokura, and Keiji Tanino
    • Journal Title

      Tetrahedron Letters

      Volume: 58 Issue: 12 Pages: 1223-1226

    • DOI

      10.1016/j.tetlet.2017.02.023

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthetic Studies on Psiguadial B: Construction of Bicyclo[4.3.1]decane Skeleton via Double Cyclization Reaction of Alkyne Dicobalt Complex2017

    • Author(s)
      Masahiko Kinebuchi, Ryohei Uematsu, and Keiji Tanino
    • Journal Title

      Tetrahedron Letters

      Volume: 58 Issue: 14 Pages: 1382-1386

    • DOI

      10.1016/j.tetlet.2017.02.058

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Non-reductive Decyanation Reactions of Disubstituted Malononitrile Derivatives Promoted by NaHMDS2017

    • Author(s)
      Daisuke Domon, Masaru Iwakura, and Keiji Tanino
    • Journal Title

      Tetrahedron Letters

      Volume: 58 Issue: 20 Pages: 1957-1960

    • DOI

      10.1016/j.tetlet.2017.04.012

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthetic Studies on Enfumafungin: Stereoselective Synthesis of the CD Ring Segment2016

    • Author(s)
      Manabu Fujitani and Keiji Tanino
    • Journal Title

      Tetrahedron Letters

      Volume: 57 Issue: 43 Pages: 4838-4841

    • DOI

      10.1016/j.tetlet.2016.09.057

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthetic Studies on Azadirachtin: Construction of the ABC Ring System via the Diels-Alder Reaction of a Vinyl Allenylsilane Derivative2015

    • Author(s)
      Kentaro Sakurai and Keiji Tanino
    • Journal Title

      Tetrahedron Letters

      Volume: 56 Issue: 3 Pages: 496-499

    • DOI

      10.1016/j.tetlet.2014.12.062

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of yellow and red fluorescent 1,3a,6a-triazapentalenes and the theoretical investigation of their optical properties2015

    • Author(s)
      Kosuke Namba, Ayumi Osawa, Akira Nakayama, Akane Mera, Fumi Tano, Yoshiro Chuman, Eri Sakuda, Tetsuya Taketsugu, Kazuyasu Sakaguchi, Noboru Kitamura, Keiji Tanino
    • Journal Title

      Chemical Science

      Volume: 6 Issue: 2 Pages: 1083-1093

    • DOI

      10.1039/c4sc02780a

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Acid-catalyzed [4+3] cycloaddition reaction of N-nosyl pyrroles2015

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

      Tetrahedron

      Volume: 71 Issue: 26-27 Pages: 4495-4499

    • DOI

      10.1016/j.tet.2015.02.071

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Novel Inhibitors Targeting PPM1D Phosphatase Potently Suppress Cancer Cell Proliferation.2015

    • Author(s)
      Ogasawara, S., Kiyota, Y., Chuman, Y., Kowata, A., Yoshimura, F., Tanino, K., Kamada, R., and Sakaguchi, K.
    • Journal Title

      Bioorg. Med. Chem.

      Volume: 23 Issue: 19 Pages: 6246-6249

    • DOI

      10.1016/j.bmc.2015.08.042

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Total Synthesis of Palau’amine2015

    • Author(s)
      K. Namba, K. Takeuchi, Y. Kaihara, M. Oda, A. Nakayama, A. Nakayama, M. Yoshida, and K. Tanino
    • Journal Title

      Nature Communications

      Volume: 6 Issue: 1 Pages: 8731-8731

    • DOI

      10.1038/ncomms9731

    • NAID

      120006999407

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Presentation] 多環性天然物ソラノエクレピンAの不斉全合成2018

    • Author(s)
      谷野 圭持
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] シアノ基の特性を活用した炭素-炭素結合形成法の開発2017

    • Author(s)
      谷野 圭持
    • Organizer
      平成29年度前期(春季)有機合成化学講習会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] シアノ基の特性を活用した天然物合成2017

    • Author(s)
      谷野 圭持
    • Organizer
      第52回天然物化学談話会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] シストセンチュウふ化促進物質の化学合成2017

    • Author(s)
      谷野 圭持
    • Organizer
      近畿化学協会合成部会フロー・マイクロ合成研究会 第31回公開講演会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] ふ化促進物質の全合成とジャガイモシストセンチュウ類防除へ向けた実用化研究2017

    • Author(s)
      谷野 圭持
    • Organizer
      日本線虫学会第25回大会(札幌大会)
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 有機合成の力で天然物を新世代の農薬にする2017

    • Author(s)
      谷野 圭持
    • Organizer
      第7回CSJ化学フェスタ2017
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Natural Product Synthesis by Utilizing the Cascade Reactions of Alkyne Dicobalt Complexes2016

    • Author(s)
      Keiji Tanino
    • Organizer
      The 10th International Symposium on Integrated Synthesis
    • Place of Presentation
      淡路夢舞台国際会議場(兵庫県・淡路市)
    • Year and Date
      2016-11-18
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 全合成の現場から:誰のための反応開発か?2016

    • Author(s)
      谷野圭持
    • Organizer
      第42回反応と合成の進歩シンポジウム
    • Place of Presentation
      清水文化会館マリナート(静岡県・静岡市)
    • Year and Date
      2016-11-08
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Total Synthesis of Complex Polycyclic Natural Compounds2016

    • Author(s)
      Keiji Tanino
    • Organizer
      Peking University & Hokkaido University Joint Seminar on Organic Chemistry and Chemical Biology
    • Place of Presentation
      北京大学(中国・北京市)
    • Year and Date
      2016-05-26
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Total Synthesis of Complex Polycyclic Natural Compounds2016

    • Author(s)
      Keiji Tanino
    • Organizer
      The 12th International Symposium on Organic Reactions
    • Place of Presentation
      京都テルサ(京都府・京都市)
    • Year and Date
      2016-04-22
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Asymmetric Total Synthesis of Complex Polycyclic Natural Products2015

    • Author(s)
      Keiji Tanino
    • Organizer
      The 25th Symposium on Optically Active Compounds
    • Place of Presentation
      日本薬学会館長井ホール(東京都・渋谷区)
    • Year and Date
      2015-11-27
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Total Synthesis of Complex Polycyclic Natural Products2015

    • Author(s)
      Keiji Tanino
    • Organizer
      The 3rd International Symposium on Ambitious Leader’s Program Fostering Future Leaders to Open New Frontiers in Material Science
    • Place of Presentation
      北海道大学鈴木ホール(北海道・札幌市)
    • Year and Date
      2015-11-18
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited

URL: 

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

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi