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2008 Fiscal Year Final Research Report

Asymmetric Total Synthesis of Medium-sized Lactones Using Rapid Cyclization

Research Project

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Project/Area Number 17350023
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionTokyo University of Science

Principal Investigator

SHIINA Isamu  Tokyo University of Science, 理学部, 教授 (40246690)

Project Period (FY) 2005 – 2008
Keywordsラクトン / 中員環 / 不斉全合成
Research Abstract

置換安息香酸無水物を脱水縮合剤として用いる迅速閉環反応、ならびに不斉アルドール反応を鍵工程とすることにより、9員環ラクトンであるボトシノリド類の不斉全合成を達成し、さらに8員環ラクトンであるアスタコラクチンの主骨格形成を実現した。引き続き、ボトシノリド類の構造修正体であるボトシニン酸とその類縁体の不斉全合成も完了し、イネいもち病菌に対する抗菌剤開発の端緒を切り開くことに成功した

  • Research Products

    (26 results)

All 2009 2008 2007 2006 Other

All Journal Article (10 results) Presentation (12 results) Book (2 results) Remarks (2 results)

  • [Journal Article] Chemistry and Structural Determination of Botcinolides2009

    • Author(s)
      Botcinins, and Botcinic Acids, Isamu SHIINA and Hiroki FUKUI
    • Journal Title

      Chemical Communications

      Pages: 385-400

  • [Journal Article] Total Synthesis and the Confirmation of the Revised Structures of Botcinins A and B2009

    • Author(s)
      Hiroki FUKUI, Keisuke TSUJI, Yuma UMEZAKI, andIsamu SHIINA
    • Journal Title

      Heterocycles 79

      Pages: 403-410

  • [Journal Article] Asymmetric Total Synthesis of Botcinic Acid and Its Derivatives : Synthetic Revision ofthe Structure of Botcinolides2008

    • Author(s)
      Hiroki FUKUI, Seiichi HITOMI, Ryo-suke SUZUKI, TatsuhikoIKEDA, Yuma UMEZAKI, Keisuke TSUJI, andIsamu SHIINA
    • Journal Title

      Tetrahedron Letters 49

      Pages: 6514-6517

  • [Journal Article] Asymmetric Total Synthesis of Botcinins C, D, and F2008

    • Author(s)
      Hiroki FUKUI and Isamu SHIINA
    • Journal Title

      Organic Letters 10

      Pages: 3153-3156

  • [Journal Article] Total Synthesis of 2-Hydroxytetracosanolide and 2-Hydroxy-24-oxooctacosanolide Using anEffective Lactonization2008

    • Author(s)
      Isamu SHIINA, Akane SASAKI, Takaaki KIKUCHI, and Hiroki FUKUI
    • Journal Title

      Chemistry-an Asian Journal 3

      Pages: 462-472

  • [Journal Article] Synthesis of Lactones Using Substituted Benzoic Anhydride as a Coupling Reagent2007

    • Author(s)
      Isamu SHIINA, Hiroki FUKUI, and Akane SASAKI
    • Journal Title

      Nature Protocols 2

      Pages: 2312-2317

  • [Journal Article] Total Synthesis of Natural 8- and 9- Membered Lactones : Recent Advancements inMedium-Sized Ring Formation2007

    • Author(s)
      Isamu SHIINA
    • Journal Title

      Chemical Reviews 107

      Pages: 239-273

  • [Journal Article] Stereoselective Total Synthesis of the Proposed Structure of 2-Epibotcinolide2006

    • Author(s)
      Isamu SHIINA, Yu-ji TAKASUNA, Ryo-suke SUZUKI,Hiromi OSHIUMI, Yuri KOMIYAMA, SeiichiHITOMI, and Hiroki FUKUI
    • Journal Title

      Organic Letters 8

      Pages: 5279-5282

  • [Journal Article] The First Total Synthesis of(-)and(+)-2-Hydroxy-24-oxooctacosanolide Using anEffective Lactonization2006

    • Author(s)
      Isamu SHIINA, Takaaki KIKUCHI, and Akane SASAKI
    • Journal Title

      Organic Letters 8

      Pages: 4955-4958

  • [Journal Article] Synthesis of (9E)-Isoambrettolide, a Macrocyclic Musk Compound, Using the Effective Lactonization Promoted by SymmetricBenzoic Anhydrides with Basic Catalysts2006

    • Author(s)
      Isamu SHIINA and Minako HASHIZUME
    • Journal Title

      Tetrahedron 62

      Pages: 7934-7939

  • [Presentation] ボトシニンAおよびBの不斉全合成2009

    • Author(s)
      椎名勇(他3名)
    • Organizer
      日本化学会第89春季年会
    • Year and Date
      2009-03-30
  • [Presentation] ボトシニンD類縁体の合成ならびに抗菌活性2009

    • Author(s)
      椎名勇(他2名)
    • Organizer
      日本化学会第89春季年会
    • Year and Date
      2009-03-30
  • [Presentation] ペルオキシボトシニンDの不斉全合成2009

    • Author(s)
      椎名勇(他2名)
    • Organizer
      日本化学会第89春季年会
    • Year and Date
      2009-03-30
  • [Presentation] アスタコラクチンの全合成研究2009

    • Author(s)
      椎名勇(他2名)
    • Organizer
      日本化学会第89春季年会
    • Year and Date
      2009-03-28
  • [Presentation] 天然8員環状化合物アスタコラクチンの合成研究2008

    • Author(s)
      椎名勇(他1名)
    • Organizer
      日本化学会第88春季年会
    • Year and Date
      2008-03-29
  • [Presentation] 2-エピボトシノリドおよびボトシニンC, D, Fの不斉全合成2008

    • Author(s)
      椎名勇(他7名)
    • Organizer
      日本化学会第88春季年会
    • Year and Date
      2008-03-27
  • [Presentation] ボトシニン酸およびボトシニンEの全合成研究2008

    • Author(s)
      椎名勇(他2名)
    • Organizer
      日本化学会第88春季年会
    • Year and Date
      2008-03-27
  • [Presentation] ペルオキシボトシニン類の不斉合成研究2008

    • Author(s)
      椎名勇(他2名)
    • Organizer
      日本化学会第88春季年会
    • Year and Date
      2008-03-27
  • [Presentation] 2-エピボトチノリド提案構造の不斉合成2007

    • Author(s)
      椎名勇(他4名)
    • Organizer
      日本化学会第87春季年会
    • Year and Date
      2007-03-25
  • [Presentation] ボトチノリド類修正構造の不斉合成研究2007

    • Author(s)
      椎名勇(他4名)
    • Organizer
      日本化学会第87春季年会
    • Year and Date
      2007-03-25
  • [Presentation] MNBAを用いた高速ラクトン形成法によるボトチノリド類の合成研究2006

    • Author(s)
      椎名勇(他4名)
    • Organizer
      日本化学会第86春季年会
    • Year and Date
      2006-03-30
  • [Presentation] ボトチノリド類の側鎖の不斉合成ならびに9員環ラクトン部とのカップリング反応2006

    • Author(s)
      椎名勇(他3名)
    • Organizer
      日本化学会第86春季年会
    • Year and Date
      2006-03-30
  • [Book] New Acid Catalysis for Modern Organic Chemistry(2)2008

    • Author(s)
      Isamu SHIINA and Hiroki HUKUI
    • Total Pages
      517-550
    • Publisher
      Wiley-VCH
  • [Book] Electronic Encyclopedia of Reagents for Organic Synthesis(10)2008

    • Author(s)
      Isamu SHIINA
    • Total Pages
      1-30
    • Publisher
      2-Methyl-6-nitrobenzoic Anhydride (MNBA)
  • [Remarks] Banyu Young Chemist Award 2006((財)万有生命科学振興国際交流財団)

  • [Remarks]

    • URL

      http://www.sut.ac.jp/fac/teacher/index.php?A06637

URL: 

Published: 2010-06-10   Modified: 2016-04-21  

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