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2011 Fiscal Year Final Research Report

Total Synthesis of Biologically Active Compounds Based on the the Cascade-Type Sigmatropic Rearrangements

Research Project

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Project/Area Number 20350021
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionKeio University

Principal Investigator

CHIDA Noritaka  慶應義塾大学, 理工学部, 教授 (50197612)

Project Period (FY) 2008 – 2011
Keywordsシグマトロピー転位 / Claisen転位 / Overman転位 / カスケード型転位 / モルヒネ / アゲラスタチンA / カイニン酸 / ブロッソネチン
Research Abstract

Development of the cascade-type sigmatropic rearrangements of chiral allylic vicinal diol compounds which generates new C-C or C-N bonds via chirality transfer of C-O bonds of the substrate has been investigated. Biologically active compounds such as morphine and agelastatin A were successfully synthesized using the cascade-type Claisen and Overman rearrangements. The orthoamide-type Claisen and Overman rearrangements, which required no protecting group manipulation, were also developed. Based on the orthoamide-type rearrangement, effective total syntheses of kainic acid and broussonetine F were achieved.

  • Research Products

    (13 results)

All 2011 2010 2009 2008 Other

All Journal Article (5 results) (of which Peer Reviewed: 5 results) Presentation (6 results) Book (1 results) Remarks (1 results)

  • [Journal Article] Total Synthesis of Broussonetine F : The Orthoamide Overman Rearrangement of an Allylic Diol2011

    • Author(s)
      Naoto Hama, Toshihiko Aoki, Shohei Miwa, Miki Yamazaki, Takaaki Sato, Noritaka Chida
    • Journal Title

      Organic Letters

      Volume: 13 Pages: 616-619

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

    • Author(s)
      Katsunori Kitamoto, Mana Sampei, Yasuaki Nakayama, Takaaki Sato, Noritaka Chida
    • Journal Title

      Organic Letters

      Volume: 12 Pages: 5756-5759

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

    • Author(s)
      Naoto Hama, Tomoki Matsuda, Takaaki Sato, Noritaka Chida
    • Journal Title

      Organic Letters

      Volume: 11 Pages: 2687-2690

    • Peer Reviewed
  • [Journal Article] Total Synthesis of A-315675 Based on the Cascade Overman Rearrangement2008

    • Author(s)
      Takayuki Momose, Naoto Hama, Chiharu Higashino, Hideyuki Sato, Noritaka Chida
    • Journal Title

      Tetrahedron Letters

      Volume: 49 Pages: 1376-1379

    • Peer Reviewed
  • [Journal Article] Formal Synthesis of (-)-Morphine from D-Glucal Based on the Cascade Claisen Rearrangement2008

    • Author(s)
      Hiroki Tanimoto, Ryosuke Saito, Noritaka Chida
    • Journal Title

      Tetrahedron Letters

      Volume: 49 Pages: 358-362

    • Peer Reviewed
  • [Presentation] 光学活性なアリルジオールに対する連続的シグマトロピー転位2011

    • Author(s)
      中山泰彰, 北元克典, 三瓶真菜, 佐藤隆章, 千田憲孝
    • 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
    • Year and Date
      2011-11-19
  • [Presentation] 連続的シグマトロピー転位の開発とカイノイド類全合成への応用2011

    • Author(s)
      北元克典, 三瓶真菜, 中山泰彰, 市來政人, 佐藤隆章, 千田憲孝
    • Organizer
      第53回天然有機化合物討論会
    • Place of Presentation
      大阪国際交流センター
    • Year and Date
      2011-09-28
  • [Presentation] ワンポット連続反応を利用した生物活性アルカロイドの合成研究2010

    • Author(s)
      千田憲孝
    • Organizer
      日本化学会第4回関東支部大会
    • Place of Presentation
      筑波大学
    • Year and Date
      2010-08-30
  • [Presentation] Total Synthesis of Biologically Active Alkaloids Based on the Cascade Sigmatropic Rearrangement2010

    • Author(s)
      Noritaka Chida
    • Organizer
      The 11th Florida Heterocyclic and Synthetic Conference
    • Place of Presentation
      フロリダ大学(米国)
    • Year and Date
      2010-03-09
  • [Presentation] Synthetic Study of (-)-Kainic Acid via Sequential Claisen-Overman Rearrangement2009

    • Author(s)
      Katsunori Kitamoto, Mana Sampei, Takaaki Sato, Noritaka Chida
    • Organizer
      The 11th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      リーガロイヤルホテル京都
    • Year and Date
      2009-11-11
  • [Presentation] Overman転位ならびにそのカスケード型反応を利用した生物活性アルカロイド類の全合成2009

    • Author(s)
      濱直人, 松田知樹, 三輪祥平, 佐藤隆章, 千田憲孝
    • Organizer
      第51回天然有機化合物討論
    • Place of Presentation
      名古屋市公会堂
    • Year and Date
      2009-10-08
  • [Book] Chemistry of Opioids2011

    • Author(s)
      Noritaka Chida
    • Total Pages
      1-28
    • Publisher
      Springer
  • [Remarks] 千田研究室ホームページ

    • URL

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

URL: 

Published: 2013-07-31  

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