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Synthetic studies toward strictamine of natural products via an indolenine as a key intermediate

Research Project

Project/Area Number 26870101
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Chemical pharmacy
Research InstitutionChiba University

Principal Investigator

Kagawa Natsuko  千葉大学, 環境健康フィールド科学センター, 講師 (60467686)

Research Collaborator Rawal Viresh H.  The University of Chicago, Professor
Project Period (FY) 2014-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2016: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2015: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2014: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywords天然物 / 生合成 / インドールアルカロイド / Mitsunobu反応 / インドレニン / パラジウム触媒 / ニトリル / 国際共同研究 / Mitsunobu法 / 全合成 / アリル化反応 / 光延反応 / モノアミンオキシダーゼ阻害 / 国際情報交換(米国) / 天然物合成 / ヨウ素NMR
Outline of Final Research Achievements

This research project was a chemical study to explore how to efficiently synthesize strictamine which was a phytochemical expected to have a strong effect on cranial nerves. The molecular structure of strictamine has a characteristic skeleton of an indolenine, which is sensitive to many chemical reactions. Therefore, we made a strategy to build the indolenine at the final stage and developed a synthetic route. In addition, we succeeded in developing a novel method, one-carbon homologation of primary alcohols to carboxylic acids, esters, and amides via MAC-Mitsunobu reaction, that achieved its one-pot conversion of two steps instead of conventional four-steps' conversion. Application of this method to industry might result in considerable reduction of efforts and cost.

Report

(5 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (36 results)

All 2018 2017 2016 2015 2014 Other

All Int'l Joint Research (3 results) Journal Article (11 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 8 results,  Open Access: 1 results,  Acknowledgement Compliant: 4 results) Presentation (17 results) (of which Int'l Joint Research: 4 results) Remarks (5 results)

  • [Int'l Joint Research] The University of Chicago(米国)

    • Related Report
      2017 Annual Research Report
  • [Int'l Joint Research] The University of Chicago(米国)

    • Related Report
      2016 Research-status Report
  • [Int'l Joint Research] The University of Chicago(米国)

    • Related Report
      2015 Research-status Report
  • [Journal Article] Growth and nutrient level in water spinach (Ipomoea aquatica Forsk.) in response to LED light quality in plant factory2018

    • Author(s)
      Jarinee Khwankaew, Duyen T.P. Nguyen, Natsuko Kagawa, Michiko Takagaki, Gauri Maharjan, Na Lu
    • Journal Title

      Acta Horticulturae

      Volume: 印刷中

    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Journal Article] Concise approach to mono- and disubstituted luotonin A analogs and their cytotoxicity test2018

    • Author(s)
      Natsuko Kagawa, Kimiko Nishimura, Shinya Abe, Takashi Masuko, Masahiro Toyota
    • Journal Title

      Heterocycles

      Volume: 印刷中 Issue: 1 Pages: 514-514

    • DOI

      10.3987/com-17-s(t)6

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 高度環境制御下の薬効成分の応答2018

    • Author(s)
      加川夏子
    • Journal Title

      アグリバイオ

      Volume: 2 Pages: 13-16

    • Related Report
      2017 Annual Research Report
  • [Journal Article] 人工光の波長でみる植物の代謝変化2018

    • Author(s)
      魯娜、加川夏子
    • Journal Title

      アグリバイオ

      Volume: 2 Pages: 37-38

    • Related Report
      2017 Annual Research Report
  • [Journal Article] Growth and Accumulation of Secondary Metabolites in Perilla as Affected by Photosynthetic Photon Flux Density and Electrical Conductivity of the Nutrient Solution2017

    • Author(s)
      Lu Na、Bernardo Emmanuel L.、Tippayadarapanich Chayanit、Takagaki Michiko、Kagawa Natsuko、Yamori Wataru
    • Journal Title

      Frontiers in Plant Science

      Volume: 8 Pages: 708-708

    • DOI

      10.3389/fpls.2017.00708

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Synthesis of functionalized morphan scaffold via a palladium-catalized cycloalkenylation and Beckmann rearrangement2017

    • Author(s)
      Natsuko Kagawa, Yutaka Yamamoto, Shuichiro Ono, Masahiro Toyota
    • Journal Title

      Heterocycles

      Volume: 印刷中

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] One-carbon homologation of primary alcohols to carboxylic acids, esters, and amides via Mitsunobu reactions with MAC reagents2016

    • Author(s)
      Natsuko Kagawa, Antoinette E. Nibbs, Viresh H. Rawal
    • Journal Title

      Organic Letters

      Volume: 18 Issue: 10 Pages: 2363-2366

    • DOI

      10.1021/acs.orglett.6b00790

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Construction of Bicyclo[3.2.1]octane System Carrying (R)-Carvone Core under Oxidative Radical Conditions: Synthetic Access to (+)-Miroestrols.2015

    • Author(s)
      M. Hamano, M. Akimoto, K. Funada, N. Kagawa, N. Suzuki, T. Ishikawa
    • Journal Title

      Synlett

      Volume: 26 Issue: 04 Pages: 547-551

    • DOI

      10.1055/s-0034-1379700

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Characterization of organic iodides with iodine-127 nuclear magnetic resonance spectroscopy2015

    • Author(s)
      N. Kagawaa, M. Suzuki, N. Kogure, K. Toume
    • Journal Title

      Tetrahedron Lett.

      Volume: 56 Issue: 42 Pages: 5795-5798

    • DOI

      10.1016/j.tetlet.2015.09.016

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of 3'-allylindoline spirobenzopyrans derived from 3-allyl-3H-indoles2014

    • Author(s)
      Natsuko Kagawa, Hiroki Takabatake, Yoshitake Masuda
    • Journal Title

      Tetrahedron Letters

      Volume: 55 Issue: 47 Pages: 6427-6431

    • DOI

      10.1016/j.tetlet.2014.09.121

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Rare earth triflates/chlorotrimethylsilane-promoted one-pot synthesis of enals2014

    • Author(s)
      Natsuko Kagawa, Yoshiko Sasaki, Shoko Sakaguchi, Ayumi Nagatomo, Hideo Kojima, Masahiro Toyota
    • Journal Title

      Heterocycles

      Volume: 88 Issue: 2 Pages: 1581-1585

    • DOI

      10.3987/com-13-s(s)98

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Presentation] ストレスに応答した青シソ二次代謝関連遺伝子の発現制御2018

    • Author(s)
      平安山昌史、井口広也、加川夏子、華岡光正
    • Organizer
      日本農芸化学会2018年度大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Effects of cutting and drying leaves of culinary herbs on contents of bioactive phytochemicals in Perilla frutescens2018

    • Author(s)
      Natsuko Kagawa, Masahumi Henzan, Hiroya Iguchi, Mitsumasa Hanaoka
    • Organizer
      255th ACS National Meeting
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Growth and nutrient level in water spinach (Ipomoea aquatica Forsk.) in response to LED light quality in plant factory2017

    • Author(s)
      Jarinee Khwankaew, Duyen T.P. Nguyen, Natsuko Kagawa, Michiko Takagaki, Gauri Maharjan, Na Lu
    • Organizer
      GREENSYS2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 植物工場技術によるシソ生理活性物質の制御について2017

    • Author(s)
      加川夏子, 魯 娜, 高垣美智子
    • Organizer
      日本生薬学会第64回年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 環境変化に対する薬用植物の代謝応答について2017

    • Author(s)
      加川夏子
    • Organizer
      2017年度千葉大学グローバルプロミネント研究基幹シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] Changes in phytochemical contents of Perilla frutescens grown in a plant factory under controlled environmental conditions2017

    • Author(s)
      Natsuko Kagawa, Na Lu
    • Organizer
      31st EFFoST International Conference (The European Federation of Food Science and Technology)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 青シソの二次代謝関連遺伝子発現のストレス応答2017

    • Author(s)
      井口広也、平安山昌史、加川夏子、華岡光正
    • Organizer
      日本植物学会第81回大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] アルコールからの1炭素伸長エステル・アミド・カルボン酸の合成法の開発2016

    • Author(s)
      加川夏子, Antoinette E. Nibbs, Viresh H. Rawal
    • Organizer
      第42回反応と合成の進歩シンポジウム
    • Place of Presentation
      静岡市清水文化会館 マリナート(静岡県静岡市)
    • Year and Date
      2016-11-07
    • Related Report
      2016 Research-status Report
  • [Presentation] Quantitative chemical analysis of bioactive extracts from leaves of Perilla frutescens grown in a plant factory with different light intensities and nutrient levels2016

    • Author(s)
      Natsuko Kagawa, Na Lu, Chayanit Tippayadarapanich, Michiko Takagaki, Wataru Yamori
    • Organizer
      The First Food Chemistry Conference
    • Place of Presentation
      HN Hotel Krasnapolsky (オランダ、アムステルダム)
    • Year and Date
      2016-11-01
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] 植物工場で環境ストレスを与えて生育したシソに蓄積する二次代謝産物の定量解析2016

    • Author(s)
      加川夏子、魯 娜、矢守航
    • Organizer
      第21回天然薬物の開発と応用シンポジウム
    • Place of Presentation
      千葉大学薬学部120周年記念講堂(千葉県千葉市)
    • Year and Date
      2016-10-28
    • Related Report
      2016 Research-status Report
  • [Presentation] 植物工場でストレスを与えたシソの生育および薬用成分の変化2016

    • Author(s)
      加川夏子、魯 娜、Chayanit Tippayadarapanich,、高垣美智子、矢守航
    • Organizer
      日本生薬学会第63回年会
    • Place of Presentation
      富山国際会議場(富山県富山市)
    • Year and Date
      2016-09-24
    • Related Report
      2016 Research-status Report
  • [Presentation] 吃逆治療薬シテイ煎じ液の院内製剤における安定性評価2016

    • Author(s)
      佐竹尚子、加川夏子、宮澤正幸、関根祐子
    • Organizer
      第26回日本医療薬学会年会
    • Place of Presentation
      国立京都国際会館(京都府京都市)
    • Year and Date
      2016-09-17
    • Related Report
      2016 Research-status Report
  • [Presentation] 有機化合物のためのヨウ素127-NMR同定法2016

    • Author(s)
      加川夏子、鈴木優章、小暮紀行、當銘一文
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Year and Date
      2016-03-28
    • Related Report
      2015 Research-status Report
  • [Presentation] 有機ヨウ素化合物のためのヨウ素127-NMR同定法2015

    • Author(s)
      加川夏子、鈴木優章、小暮紀行、當銘一文
    • Organizer
      第18回 ヨウ素学会シンポジウム
    • Place of Presentation
      千葉大学けやき会館(千葉県千葉市)
    • Year and Date
      2015-09-16
    • Related Report
      2015 Research-status Report
  • [Presentation] シテイ煎じ法の違いによるトリテルペン含量の変化2015

    • Author(s)
      加川夏子、佐竹尚子、関根祐子
    • Organizer
      日本生薬学会 第62回年会
    • Place of Presentation
      長良川国際会議場(岐阜県岐阜市)
    • Year and Date
      2015-09-12
    • Related Report
      2015 Research-status Report
  • [Presentation] 異なる光強度と培養液濃度がアカジソの生育およびペリルアルデヒド含有量に及ぼす影響2015

    • Author(s)
      魯 娜、Emmanuel Bernardo、高垣 美智子、加川 夏子、矢守 航
    • Organizer
      日本生薬学会 第62回年会
    • Place of Presentation
      長良川国際会議場(岐阜県岐阜市)
    • Year and Date
      2015-09-12
    • Related Report
      2015 Research-status Report
  • [Presentation] 新規3'-アリルインドリン スピロベンゾピラン類の合成とUVA応答性の調査2014

    • Author(s)
      加川夏子,高畠弘樹,Ade Arsianti,増田佳丈
    • Organizer
      第40回反応と合成の進歩シンポジウム
    • Place of Presentation
      東北大学(宮城県仙台市)
    • Year and Date
      2014-11-11
    • Related Report
      2014 Research-status Report
  • [Remarks] Organic Chemistry Portal

    • URL

      http://www.organic-chemistry.org/abstracts/lit5/421.shtm

    • Related Report
      2017 Annual Research Report
  • [Remarks] 千葉大学戦略的重点研究強化プログラム ファイトケミカル植物分子科学

    • URL

      http://www.p.chiba-u.jp/phytochemical/index.html

    • Related Report
      2017 Annual Research Report
  • [Remarks] ファイトケミカル植物分子科学

    • URL

      http://www.p.chiba-u.jp/phytochemical/

    • Related Report
      2016 Research-status Report
  • [Remarks] 国立大学法人 千葉大学 テニュアトラック制 教員紹介

    • URL

      http://www.chiba-u.ac.jp/tenure/researchers/index.html

    • Related Report
      2015 Research-status Report
  • [Remarks] 千葉大学 テニュアトラック制 TT教員pickup!

    • URL

      http://www.chiba-u.ac.jp/tenure/TTpickup/Kagawa.html

    • Related Report
      2014 Research-status Report

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Published: 2014-04-04   Modified: 2022-06-07  

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