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Synthetic studies on complex natural products based on development of a novel indole synthesis

Research Project

Project/Area Number 18K14862
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 47010:Pharmaceutical chemistry and drug development sciences-related
Research InstitutionTohoku University

Principal Investigator

Sakata Juri  東北大学, 薬学研究科, 助教 (20772700)

Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2020: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2019: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2018: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywords全合成 / インドール / アルカロイド / デュオカルマイシン / (+)-CC-1065 / ピロロイミノキノン / CC-1065 / オキシム / ベンゾシクロブテノン / イソバゼリン / バゼリン / アマニチン / インドール合成法 / ディスコハブディン / オキシムスルホナート
Outline of Final Research Achievements

Synthetic studies on pharmacologically important and highly functionalized indole alkaroids were conducted based on a novel indole synthesis utilizing ring expansion reaction of oxide sulfonate. As results, we established synthetic route toward CC-1065, isobatzelline A/B, and batzelline A. We also developed the synthetic method for other pharmacologically important alkaloids, Lepadiformine, emestrin H, and asteroxepin.

Academic Significance and Societal Importance of the Research Achievements

近年、医薬リードの枯渇から複雑天然物の構造展開により創薬を行う重要性が再認識されている。この背景から、複雑なsp3炭素の縮環構造に組み込まれた全置換ベンゼン、酸素や窒素、硫黄などのヘテロ官能基を多数有するなど、一筋縄では合成できない多置換インドールアルカロイドの合成研究が近年の創薬研究において重要視されている。このような背景を踏まえ、本研究では構造的に複雑かつ医薬リードとして魅力的なインドールアルカロイドの全合成研究に取り組み、その効率的合成法を確立した。

Report

(4 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Research-status Report
  • 2018 Research-status Report
  • Research Products

    (23 results)

All 2020 2019 2018

All Journal Article (8 results) (of which Peer Reviewed: 8 results) Presentation (15 results) (of which Int'l Joint Research: 3 results)

  • [Journal Article] Cyclic Sulfamidite as Simultaneous Protecting Group for Amino Alcohols: Development of a Mild Deprotection Protocol Using Thiophenol2020

    • Author(s)
      Sakata Juri、Akita Kazunari、Sato Manabu、Shimomura Masashi、Tokuyama Hidetoshi
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 68 Issue: 10 Pages: 996-1000

    • DOI

      10.1248/cpb.c20-00531

    • NAID

      130007920334

    • ISSN
      0009-2363, 1347-5223
    • Year and Date
      2020-10-01
    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Divergent Total Syntheses of Isobatzellines A/B and Batzelline A2020

    • Author(s)
      Yamashita Yumi、Poignant Louna、Sakata Juri、Tokuyama Hidetoshi
    • Journal Title

      Organic Letters

      Volume: 22 Issue: 16 Pages: 6239-6243

    • DOI

      10.1021/acs.orglett.0c01894

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total syntheses of (-)-emestrin H and (-)-asteroxepin2020

    • Author(s)
      Umeki Kanato、Ueda Yusuke、Sakata Juri、Tokuyama Hidetoshi
    • Journal Title

      Tetrahedron

      Volume: 76 Issue: 48 Pages: 131630-131630

    • DOI

      10.1016/j.tet.2020.131630

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of (?)-Lepadiformine A via Radical Translocation?Cyclization Reaction2020

    • Author(s)
      Shimomura Masashi、Sato Manabu、Azuma Hiroki、Sakata Juri、Tokuyama Hidetoshi
    • Journal Title

      Organic Letters

      Volume: 22 Issue: 9 Pages: 3313-3317

    • DOI

      10.1021/acs.orglett.0c00474

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Fluorescent Labeling Method Re-Evaluates the Intriguing Thermoresponsive Behavior of Poly(acrylamide-co-acrylonitrile)s with Upper Critical Solution Temperatures2019

    • Author(s)
      Otsuka Chie、Wakahara Yuko、Okabe Kohki、Sakata Juri、Okuyama Masaki、Hayashi Akinobu、Tokuyama Hidetoshi、Uchiyama Seiichi
    • Journal Title

      Macromolecules

      Volume: 52 Issue: 20 Pages: 7646-7660

    • DOI

      10.1021/acs.macromol.9b00880

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of (+)-CC-1065 Utilizing Ring Expansion Reaction of Benzocyclobutenone Oxime Sulfonate2019

    • Author(s)
      Imaizumi Taku、Yamashita Yumi、Nakazawa Yuki、Okano Kentaro、Sakata Juri、Tokuyama Hidetoshi
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 16 Pages: 6185-6189

    • DOI

      10.1021/acs.orglett.9b01690

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthetic Studies on Plakinidines2019

    • Author(s)
      Tokuyama Hidetoshi、Satoh Takahito、Adachi Touma、Sakata Juri、Okano Kentaro
    • Journal Title

      HETEROCYCLES

      Volume: 99 Issue: 1 Pages: 310-310

    • DOI

      10.3987/com-18-s(f)26

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] One-Pot Reductive Allylation of Amides by Using a Combination of Titanium Hydride and an Allylzinc Reagent: Application to a Total Synthesis of (?)-Castoramine2018

    • Author(s)
      Tokuyama Hidetoshi、Itabashi Suguru、Shimomura Masashi、Sato Manabu、Azuma Hiroki、Okano Kentaro、Sakata Juri
    • Journal Title

      Synlett

      Volume: 29 Issue: 13 Pages: 1786-1790

    • DOI

      10.1055/s-0037-1610435

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Presentation] Acochlearineの合成研究 (口頭)2020

    • Author(s)
      ○河野駿、宮本尚也、藤岡孝佑、坂田樹理、徳山英利
    • Organizer
      第141回日本薬学会年会, 2021年3月26-29日(広島、オンライン)28V01-am10S
    • Related Report
      2020 Annual Research Report
  • [Presentation] 海洋アルカロイドplakinidine Dの全合成および第二世代合成研究 (口頭)2020

    • Author(s)
      ○秋田 一成、安達 陶磨、野呂 尭広、坂田 樹理、徳山 英利
    • Organizer
      第141回日本薬学会年会, 2021年3月26-29日(広島、オンライン)29V01-am03S
    • Related Report
      2020 Annual Research Report
  • [Presentation] アリルオキシメチル基を用いた第二級アミドの保護/脱保護法の開発 (口頭)2020

    • Author(s)
      ○上田悠介、梅木奏利、坂田樹理、徳山英利
    • Organizer
      第59回日本薬学会東北支部大会、2020年10月18日(いわき、オンライン)
    • Related Report
      2020 Annual Research Report
  • [Presentation] Cyclic Sulfamidite as a Protecting Group for Amino Alcohols (poster)2020

    • Author(s)
      ○ Kazunari Akita, Manabu Sato, Masashi Shimomura, Juri Sakata, Hidetoshi Tokuyama
    • Organizer
      令和2年度化学系学協会東北大会, 2020年9月26-27日(青森、オンライン)PC117
    • Related Report
      2020 Annual Research Report
  • [Presentation] Protection of Diketopiperazine and Amide with Allyloxymethyl Group: Total Synthesis of Asteroxepin (Poster)2020

    • Author(s)
      ○ Yusuke Ueda, Kanato Umeki, Juri Sakata, Hidetoshi Tokuyama
    • Organizer
      令和2年度化学系学協会東北大会, 2020年9月26-27日(青森、オンライン)PC121
    • Related Report
      2020 Annual Research Report
  • [Presentation] オキシムスルホナートの環拡大反応を利用したインドール合成法を基盤とする(+)-CC-1065、isobatzelline A/B、batzelline Aの全合成 (口頭)2020

    • Author(s)
      ○ 坂田樹理、今泉 拓、山下有美、Louna Poignat、徳山英利
    • Organizer
      第62回天然物有機化合物討論会,2020年9月23日(名古屋、オンライン)
    • Related Report
      2020 Annual Research Report
  • [Presentation] Batzelline AおよびIsobatzelline A、Bの全合成 (口頭)2020

    • Author(s)
      山下有美、坂田樹理、徳山英利
    • Organizer
      第140回日本薬学会年会, 2020年3月25-28日(京都)26H-am06
    • Related Report
      2019 Research-status Report
  • [Presentation] Makaluvamine Fの全合成 (口頭)2020

    • Author(s)
      下村 誠志、坂田樹理、徳山英利
    • Organizer
      第140回日本薬学会年会, 2020年3月25-28日(京都)26H-am07S
    • Related Report
      2019 Research-status Report
  • [Presentation] Development of Novel Indole Synthesis via Ring Expansion Reaction of Benzocyclobutenone Oxime Sulfonate: Its Application to Alkaloid Synthesis2019

    • Author(s)
      Juri Sakata, Yumi Yamashita, Taku Imaizumi, Hidetoshi Tokuyama
    • Organizer
      The 18th Asian Chemical Congress, December, 2019, Taipei, Taiwan, O12-004
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] ベンゾシクロブテノンオキシムスルホナートのBeckmann開裂反応を利用したベンゾニトリル合成法の開発(ポスター)2019

    • Author(s)
      清水瑛大、坂田樹理、徳山英利
    • Organizer
      第45回反応と合成の進歩シンポジウム,2019年10月28日(倉敷
    • Related Report
      2019 Research-status Report
  • [Presentation] Total Synthesis of (+)-CC1065 via Two Directional Double Ring Expansion of Benzo-bis-Cyclobutenone Oxime Sulfonate2019

    • Author(s)
      Juri Sakata, Taku Imaizumi, Yumi Yamashita, Hidetoshi Tokuyama
    • Organizer
      The 27th International Society of Heterocyclic Chemistry Congress, September, 2019, Kyoto, Japan, 2P-141
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Development of Novel Indole Synthesis via Ring Expansion Reaction of Oxime Sulfonate: Its Application to Total Synthesis of (+)-CC-1065 and Isobatzellines2019

    • Author(s)
      Yumi Yamashita, Taku Imaizumi, Louna Poignant, Juri Sakata, Hidetoshi Tokuyama
    • Organizer
      Tohoku University's Chemistry Summer School 2019, August 27-28, 2019, Sendai, Japan, O-24
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Development of a Novel Indole Synthesis by Ring Expansion Reaction of Oxime Sulfonate and Total Synthesis of (+)-CC-10652018

    • Author(s)
      Yumi Yamashita, Taku Imaizumi, Juri Sakata, Hidetoshi Tokuyama
    • Organizer
      The Third A3 Roundtable Meeting on Chemical Probe Research Hub
    • Related Report
      2018 Research-status Report
  • [Presentation] オキシムスルホナートの環拡大反応による新規インドール合成法の開発とその応用2018

    • Author(s)
      山下有美,今泉拓,坂田樹理,徳山英利
    • Organizer
      第48回複素環化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] Total Synthesis of (+)-CC-1065 Utilizing Ring Expansion Reaction of Benzocyclobutenone Oxime Sulfonates2018

    • Author(s)
      Taku Imaizumi, Yumi Yamashita, Juri Sakata, Hidetoshi Tokuyama
    • Organizer
      第2回 A3若手研究者ミーティング
    • Related Report
      2018 Research-status Report

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Published: 2018-04-23   Modified: 2022-01-27  

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