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Development and Application of Practical Methodology to Access Biologically Active Alkaloids Using Alkoxyamide

Research Project

Project/Area Number 21750049
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionKeio University

Principal Investigator

SATO Takaaki  慶應義塾大学, 理工学部, 助教 (70509926)

Project Period (FY) 2009 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2011: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2010: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2009: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywordsアミド / アルコキシアミド / 求核付加反応 / タンデム反応 / ゲフィロトキシン / Weinrebアミド / マダンガミン
Research Abstract

Amide functional groups play a significant role in a variety of areas such as medicinal drugs and chemical fibers. Therefore, organic chemists have developed the efficient synthesis of amide bonds. On the other hand, functionalization of the generated amide carbonyl groups is less explored than their construction due to the high stability of the amide. In this study, we succeeded to functionalize the amide group using the unique properties of alkoxyamides.

Report

(4 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • 2009 Annual Research Report
  • Research Products

    (33 results)

All 2012 2011 2010 2009 Other

All Journal Article (11 results) (of which Peer Reviewed: 11 results) Presentation (18 results) Book (2 results) Remarks (2 results)

  • [Journal Article] Direct Chemoselective Allylation of Inert Amide Carbonyls2012

    • Author(s)
      Oda, Y.; Sato, T.; Chida, N.
    • Journal Title

      Org. Lett

      Volume: 14 Pages: 950-953

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Direct Chemoselective Allylation of Inert Amide Carbonyls2012

    • Author(s)
      Yukiko Oda
    • Journal Title

      Organic Letters

      Volume: 14 Issue: 3 Pages: 950-953

    • DOI

      10.1021/ol3000316

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Broussonetine F : The Orthoamide Overman Rearrangement of an Allylic Diol2011

    • Author(s)
      Hama, N.; Aoki, T.; Miwa, S.; Yamazaki, M.; Sato, T.; Chida, N.
    • Journal Title

      Org. Lett

      Volume: 13 Pages: 616-619

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of(-)-Salinosporamide A2011

    • Author(s)
      Kaiya, Y.; Hasegawa, J.; Momose, T.; Sato, T.; Chida, N.
    • Journal Title

      Chem.-Asian J

      Volume: 5 Pages: 209-219

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Broussonetine F : The Orthoamide Overman Rearrangement of an Allylic Diol2011

    • Author(s)
      濱直人、青木紀裕、三輪祥平、山崎美貴、佐藤隆章、千田憲孝
    • Journal Title

      Organic Letters

      Volume: 13 Issue: 4 Pages: 616-619

    • DOI

      10.1021/ol102856j

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of (-)-Salinosporamide A2011

    • Author(s)
      海谷雄士、長谷川純一、百瀬孝幸、佐藤隆章、千田憲孝
    • Journal Title

      Chemistry-An Asian Journal

      Volume: 6 Issue: 1 Pages: 209-219

    • DOI

      10.1002/asia.201000602

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Novel Sequential Sigmatropic Rearrangements of Allylic Diols : Application to the Total Synthesis of(-)-Kainic Acid2010

    • Author(s)
      Kitamoto, K.; Sampei, M.; Nakayama, Y.; Sato, T.; Chida, N.
    • Journal Title

      Org. Lett

      Volume: 12 Pages: 5756-5759

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] A Direct Entry to Substituted N-Methoxyamines from N-Methoxyamides via N-Oxyiminium Ions2010

    • Author(s)
      Shirokane, K.; Kurosaki, Y.; Sato, T.; Chida, N
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 49 Pages: 6369-6372

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] A Direct Entry to Substituted N-Methoxyamines from N-Methoxyamides via N-Oxyiminium Ions2010

    • Author(s)
      白兼研史
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 49 Pages: 6369-6372

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Formal Synthesis of Salinosporamide A Starting from D-Glucose2009

    • Author(s)
      Momose, T.; Kaiya, Y.; Hasegawa, J.; Sato, T.; Chida, N
    • Journal Title

      Synthesis

      Pages: 2983-2991

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of(-)-Agelastatin A : The Application of a Sequential Sigmatropic Rearrangement2009

    • Author(s)
      Hama, N.; Matsuda, T.; Sato, T.; Chida, N.
    • Journal Title

      Org. Lett

      Volume: 11 Pages: 2687-2690

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Presentation] N-メトキシアミド基を用いたGephyrotoxinの合成研究2012

    • Author(s)
      白兼研史
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学(横浜)
    • Year and Date
      2012-03-27
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] N-アルコキシアミド基に対する連続的求核付加反応の開発2012

    • Author(s)
      柳田悠太
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学(横浜)
    • Year and Date
      2012-03-27
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] 不活性アミド基に対する官能基選択的な直接的アリル化反応2012

    • Author(s)
      小田友紀子
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学(横浜)
    • Year and Date
      2012-03-27
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] N-メトキシアミンを用いた多成分反応によるα-三置換アミンの合成法の開発2012

    • Author(s)
      黒崎友介
    • Organizer
      日本化学会92春季年会
    • Place of Presentation
      慶應義塾大学(横浜)
    • Year and Date
      2012-03-27
    • Related Report
      2011 Final Research Report
  • [Presentation] N-メトキシアミンを用いた多成分反応によるα-三置換アミンの合成法の開発2012

    • Author(s)
      黒崎友介
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学(横浜)
    • Year and Date
      2012-03-27
    • Related Report
      2011 Annual Research Report
  • [Presentation] 天然物の全合成研究におけるReaxys活用法2012

    • Author(s)
      佐藤隆章
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学(横浜)
    • Year and Date
      2012-03-25
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] N-メトキシアミド基を利用した連続的求核付加反応2011

    • Author(s)
      白兼研史
    • Organizer
      第55回香料・テルペンおよび精油化学に関する討論会
    • Place of Presentation
      筑波大学(つくば)
    • Year and Date
      2011-11-19
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] Direct Functionalization of Inert Amide Carbonyls2011

    • Author(s)
      Takaaki Sato
    • Organizer
      14^<th> Asian Chemical Congress
    • Place of Presentation
      Thailand(Bangkok)
    • Year and Date
      2011-09-07
    • Related Report
      2011 Final Research Report
  • [Presentation] Direct Functionalization of Inert Amide Carbonyls2011

    • Author(s)
      佐藤隆章
    • Organizer
      14^<th> Asian Chemical Congress
    • Place of Presentation
      Thailand
    • Year and Date
      2011-09-07
    • Related Report
      2011 Annual Research Report
  • [Presentation] N-アルコキシアミドを用いたGephyrotoxinの合成研究2011

    • Author(s)
      白兼研史
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学(横浜)
    • Year and Date
      2011-03-29
    • Related Report
      2011 Final Research Report
  • [Presentation] N-オキシイミニウムイオンを中間体とした含窒素四置換炭素構築法の開発2011

    • Author(s)
      黒崎友介
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学(横浜)
    • Year and Date
      2011-03-29
    • Related Report
      2011 Final Research Report
  • [Presentation] N-アルコキシアミドを用いたGephyrotoxinの合成研究2011

    • Author(s)
      白兼研史
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学横浜キャンパス
    • Year and Date
      2011-03-29
    • Related Report
      2010 Annual Research Report
  • [Presentation] N-オキシイミニウムイオンを中間体とした含窒素四置換炭素構築法の開発2011

    • Author(s)
      黒崎友介
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学横浜キャンパス
    • Year and Date
      2011-03-29
    • Related Report
      2010 Annual Research Report
  • [Presentation] N-アルコキシアミド基に対する連続的求核付加反応の開発2010

    • Author(s)
      白兼研史
    • Organizer
      第97回有機合成シンポジウム
    • Place of Presentation
      慶應義塾大学(東京都港区)
    • Year and Date
      2010-06-18
    • Related Report
      2011 Final Research Report
  • [Presentation] N-アルコキシアミド法を用いた実用的アルカロイド合成戦略の開発2010

    • Author(s)
      白兼研史
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      近畿大学(東大阪)
    • Year and Date
      2010-03-29
    • Related Report
      2011 Final Research Report
  • [Presentation] 生物活性アルカロイドの全合成を指向した新規方法論の開発2009

    • Author(s)
      佐藤隆章
    • Organizer
      2009年度若手研究者のためのセミナー
    • Place of Presentation
      東京大学(東京都文京区)
    • Year and Date
      2009-12-12
    • Related Report
      2011 Final Research Report
  • [Presentation] 生物活性アルカロイドの全合成を指向した新規方法論の開発2009

    • Author(s)
      佐藤隆章
    • Organizer
      2009年度若手研究者のためのセミナー
    • Place of Presentation
      東京大学弥生講堂
    • Year and Date
      2009-12-12
    • Related Report
      2009 Annual Research Report
  • [Presentation] N-アルコキシアミド法を用いた実用的アルカロイド合成戦略の開発2009

    • Author(s)
      佐藤隆章
    • Organizer
      第26回有機合成化学セミナー
    • Place of Presentation
      群馬県前橋市
    • Year and Date
      2009-09-16
    • Related Report
      2011 Final Research Report 2009 Annual Research Report
  • [Book] 天然物合成で活躍した反応実践のコツとポイント2011

    • Author(s)
      井上将行、佐藤隆章
    • Publisher
      化学同人
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Book] 天然物全合成の最新動向2010

    • Author(s)
      井上将行、佐藤隆章、平間正博
    • Publisher
      シーエムシー出版
    • Related Report
      2011 Final Research Report
  • [Remarks]

    • Related Report
      2011 Final Research Report
  • [Remarks]

    • URL

      http://www.applc.keio.ac.jp/~chida/index.html

    • Related Report
      2011 Annual Research Report

URL: 

Published: 2009-04-01   Modified: 2016-04-21  

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