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

Synthetic study on furofuran lignans by means of control of electronic properties of phenol

Research Project

Project/Area Number 26860013
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionUniversity of Shizuoka

Principal Investigator

Inai Makoto  静岡県立大学, 薬学部, 助教 (20621626)

Project Period (FY) 2014-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2015: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2014: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywordsセサミン / セサミノール / ヘジオトール A / 不斉アルドール反応 / フロフランリグナン / 有機触媒 / プリンセピン / プロリンアルドール / C-H挿入反応 / キノンメチド
Outline of Final Research Achievements

Furofuran lignans isolated from various vascular plants have been reported to exhibit antitumor, antioxidant, antiviral, and antihypertensive activities, as well as inhibition of low-density lipoprotein oxidation. These furofuran lignans and their derivatives are expected to be useful as lead compounds for drug development.
In this research, plant products (+)-hedyotol A, (+)-sesamin, (+)-sesaminol, (+)-methylpiperitol, (+)-aschantin, and (+)-5'-hydroxymethylpiperitol were synthesized in a highly stereocontrolled manner through proline-catalyzed cross-aldol reaction, followed by biomimetic construction of the furofuran lignan skeleton through a quinomethide intermediate.

Report

(3 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • Research Products

    (21 results)

All 2015 2014

All Journal Article (8 results) (of which Peer Reviewed: 8 results,  Open Access: 2 results,  Acknowledgement Compliant: 1 results) Presentation (13 results) (of which Invited: 1 results)

  • [Journal Article] Stereocontrolled Total Syntheses of Optically Active Furofuran Lignans2015

    • Author(s)
      M. Inai, R. Ishikawa, N. Yoshida, N. Shirakawa, Y. Akao, Y. Kawabe, T. Asakawa, M. Egi, Y. Hamashima, T. Kan
    • Journal Title

      Synthesis

      Volume: 47 Issue: 22 Pages: 3513-3521

    • DOI

      10.1055/s-0034-1378812

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthetic Studies of Fisetin, Myricetin and Nobiletin Analogs and Related Probe Molecules2014

    • Author(s)
      Aiki Hiza, Yuta Tsukaguchi, Takahiro Ogawa, Makoto Inai, Tomohiro Asakawa, Yoshitaka Hamashima, and Toshiyuki Kan
    • Journal Title

      HETEROCYCLES

      Volume: 88 Issue: 2 Pages: 1371-1371

    • DOI

      10.3987/com-13-s(s)107

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Practical synthesis of kainoids : a new chemical probe precursor and a fluorescent probe2014

    • Author(s)
      Sasaki, S.; Suzuki, H.; Ouchi, H.; Asakawa, T.; Inai, M.; Sakai, R.; Shimamoto, K.; Hamashima, Y.; Kan, T.
    • Journal Title

      Org Lett

      Volume: 16 Issue: 2 Pages: 564-7

    • DOI

      10.1021/ol403434e

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Practical Total Syntheses of Acromelic Acids A and B2014

    • Author(s)
      Hitoshi Ouchi, Aya Asahina, Tomohiro Asakawa, Makoto Inai, Yoshitaka Hamashima and Toshiyuki Kan
    • Journal Title

      Org. Lett.

      Volume: 16 Issue: 7 Pages: 1980-1980

    • DOI

      10.1021/ol500529w

    • NAID

      130005160054

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled Total Synthesis of Hedyotol A2014

    • Author(s)
      Yusuke Kawabe, Ryo Ishikawa, Yusuke Akao, Atsushi Yoshida, Makoto Inai, Tomohiro Asakawa, Yoshitaka Hamashima and Toshiyuki Kan
    • Journal Title

      Org. Lett.

      Volume: 16 Issue: 7 Pages: 1976-1976

    • DOI

      10.1021/ol500524y

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] The source of "fairy rings": 2-azahypoxanthine and its metabolite found in a novel purine metabolic pathway in plants2014

    • Author(s)
      J-H. Choi, T. Ohnishi, Y. Yamakawa, S. Takeda, S. Sekiguchi, W. Maruyama, K. Yamashita, T. Suzuki, A. Morita, T. Ikka, R. Motohashi, Y. Kiriiwa, H. Tobina, T. Asai, S. Tokuyama, H. Hirai, N. Yasuda, K. Noguchi, T. Asakawa, S. Sugiyama, T. Kan, H. Kawagishi
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 53 Issue: 6 Pages: 1552-1555

    • DOI

      10.1002/anie.201308109

    • NAID

      120006727084

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Total Syntheses of (+)-Sesamin and (+)-Sesaminol2014

    • Author(s)
      Ryo Ishikawa, Naoto Yoshida, Yusuke Akao, Yusuke Kawabe, Makoto Inai, Tomohiro Asakawa, Yoshitaka Hamashima, and Toshiyuki Kan
    • Journal Title

      Chemistry Letters

      Volume: 43 Issue: 10 Pages: 1572-1574

    • DOI

      10.1246/cl.140613

    • NAID

      130004427220

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Isolation and Total Syntheses of Cytotoxic Cryptolactones A1, A2, B1, and B2: α,β-Unsaturated δ-Lactones from a Cryptomyzus sp. Aphid.2014

    • Author(s)
      M. Horikawa, M. Inai, Y. Oguri, E. Kuroda, M. Tanaka, S. Suzuki, T. Ito, S. Takahashi, H. Kaku, and T. Tsunoda
    • Journal Title

      J. Nat. Prod.

      Volume: 77 Issue: 11 Pages: 2459-2464

    • DOI

      10.1021/np500542x

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Presentation] プリンセピンの合成研究2015

    • Author(s)
      吉田直人
    • Organizer
      日本病院薬剤師会東海ブロック・日本薬学会東海支部 合同学術大会2015
    • Place of Presentation
      名古屋
    • Year and Date
      2015-11-01
    • Related Report
      2015 Annual Research Report
  • [Presentation] 顕著な生物活性を有する天然物の全合成2015

    • Author(s)
      稲井誠
    • Organizer
      平成27年度若手研究者のためのセミナー
    • Place of Presentation
      名古屋
    • Year and Date
      2015-09-25
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] フロフラン天然物の合成研究2015

    • Author(s)
      白川奈菜
    • Organizer
      第61日本薬学会東海支部総会・大会
    • Place of Presentation
      名古屋
    • Year and Date
      2015-07-04
    • Related Report
      2015 Annual Research Report
  • [Presentation] フロフラン天然物の合成研究2015

    • Author(s)
      白川奈菜
    • Organizer
      新規素材探索研究会 第14回セミナー
    • Place of Presentation
      横浜
    • Year and Date
      2015-06-05
    • Related Report
      2015 Annual Research Report
  • [Presentation] ヘジオトール A の合成研究2014

    • Author(s)
      石川諒,河辺佑介,吉田直人,稲井誠,浅川倫宏,濱島義隆,菅敏幸
    • Organizer
      日本病院薬剤師会東海ブロック・日本薬学会東海支部 合同学術大会 2014
    • Place of Presentation
      静岡
    • Year and Date
      2014-11-09
    • Related Report
      2014 Research-status Report
  • [Presentation] Synthetic Study on Furofuran Lignans2014

    • Author(s)
      Ryo Ishikawa, Yusuke Kawabe, Yusuke Akao, Atsushi Yoshida, Makoto Inai, Tomohiro Asakawa, Yoshitaka Hamashima, Toshiyuki Kan
    • Organizer
      The 2nd International Conference on Pharma-Food
    • Place of Presentation
      Shizuoka
    • Year and Date
      2014-11-06
    • Related Report
      2014 Research-status Report
  • [Presentation] Hedyotol Aの全合成2014

    • Author(s)
      稲井誠,河辺佑介,石川諒,吉田直人,赤尾祐介,吉田篤史,浅川倫宏,濱島義隆,菅敏幸
    • Organizer
      第 44 回 複素環化学討論会
    • Place of Presentation
      札幌
    • Year and Date
      2014-09-10
    • Related Report
      2014 Research-status Report
  • [Presentation] Synthetic Study on Furofuran Lignans2014

    • Author(s)
      Ryo Ishikawa, Yusuke Kawabe, Yusuke Akao, Atsushi Yoshida, Makoto Inai, Tomohiro Asakawa, Yoshitaka Hamashima, Toshiyuki Kan:
    • Organizer
      The XXVIIth International Conference on Polyphenols & The 8th Tannin Conference
    • Place of Presentation
      Nagoya
    • Year and Date
      2014-09-05
    • Related Report
      2014 Research-status Report
  • [Presentation] フロフラン天然物の合成研究2014

    • Author(s)
      吉田直人, 河辺佑介, 石川諒,稲井誠,浅川倫宏,濱島義隆,菅敏幸
    • Organizer
      創薬懇話会 2014 in 岐阜
    • Place of Presentation
      岐阜
    • Year and Date
      2014-07-10
    • Related Report
      2014 Research-status Report
  • [Presentation] フロフラン天然物の合成研究2014

    • Author(s)
      吉田直人,河辺佑介,石川諒, 稲井誠,浅川倫宏,濱島義隆,菅敏幸
    • Organizer
      第 60 回日本薬学会東海支部総会・大会
    • Place of Presentation
      三重
    • Year and Date
      2014-07-05
    • Related Report
      2014 Research-status Report
  • [Presentation] 興味深い生物活性を有する天然物の合成研究2014

    • Author(s)
      稲井誠
    • Organizer
      第49回 天然物化学談話会
    • Place of Presentation
      岡山
    • Year and Date
      2014-07-03
    • Related Report
      2014 Research-status Report
  • [Presentation] ヘジオトール A の合成研究2014

    • Author(s)
      石川諒,河辺佑介,赤尾祐介,吉田篤史,稲井誠,浅川倫宏,濱島義隆,菅敏幸
    • Organizer
      新規素材探索研究会 第13回セミナー
    • Place of Presentation
      横浜
    • Year and Date
      2014-06-06
    • Related Report
      2014 Research-status Report
  • [Presentation] Hedyotol A の全合成2014

    • Author(s)
      河辺佑介,石川諒,吉田直人,赤尾祐介,吉田篤史,稲井誠,浅川倫宏,濱島義隆,菅敏幸
    • Organizer
      第12回次世代を担う有機化学シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2014-05-24
    • Related Report
      2014 Research-status Report

URL: 

Published: 2014-04-04   Modified: 2017-05-10  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi