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2012 Fiscal Year Final Research Report

Syntheses of novel amino acids and natural product derived from amino acid by using memory of chirality

Research Project

  • PDF
Project/Area Number 23790010
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionKyoto University

Principal Investigator

YOSHIMURA Tomoyuki  京都大学, 化学研究所, 助教 (20432320)

Project Period (FY) 2011 – 2012
Keywords合成化学
Research Abstract

Development of asymmetric intra- and intermolecular conjugate addition reaction via C-N axially chiral enolate intermediates were achieved. Multisubstituted β-lactams were prepared by using asymmetric intramolecular conjugate addition reaction. β-Lactams were converted into novel hybrid amino acid derivatives consisting of aspartic acid-glutamic acid. On the other hand, total synthesis of manzacidin A was completed by using intermolecular conjugate addition reaction.

  • Research Products

    (11 results)

All 2013 2012 2011 Other

All Journal Article (4 results) (of which Peer Reviewed: 4 results) Presentation (6 results) Remarks (1 results)

  • [Journal Article] Asymmetric Synthesis via Short-Lived Chiral Enolates with Chiral C-O axis2013

    • Author(s)
      Yoshimura, T.; Tomohara, K.; Kawabata, T
    • Journal Title

      J. Am. Chem. Soc

      Volume: 135 Pages: 7102-7105

    • DOI

      DOI:10.1021/ja4018122

    • Peer Reviewed
  • [Journal Article] Asymmetric Intermolecular Conjugate Addition of Amino Acid Derivatives via Memory of Chirality: Total Synthesis of Manzacidin A2013

    • Author(s)
      Yoshimura, T.; Kinoshita, T.; Yoshioka, H.; Kawabata, T
    • Journal Title

      Org. Lett

      Volume: 15 Pages: 864-867

    • DOI

      DOI:10.1021/ol303568f

    • Peer Reviewed
  • [Journal Article] Asymmetric Intermolecular Conjugate Addition of α-Amino Acid Derivatives via Racemization-Free Equilibrium of Intermediary Chiral Enolates2012

    • Author(s)
      Monguchi, D.; Yoshimura, T.; Irie, K.; Hayashi, K.; Majumdar, S.; Sasamori, T.; Tokitoh, N.; Kawabata, T
    • Journal Title

      Heterocycles

      Volume: 86 Pages: 1483-1494

    • DOI

      DOI:10.3987/COM-12-S(N)129

    • Peer Reviewed
  • [Journal Article] Protonation-Assisted Conjugate Addition of Enolate: Asymmetric Synthesis of Multisubstituted-β-Lactams from α-Amino Acids via Memory of Chiralty2012

    • Author(s)
      Yoshimura, T.; Takuwa, M.; Tomohara, K.; Uyama, M.; Hayashi, K.; Yang, P.; Hyakutake, R.; Sasamori, Y.; Tokitoh, N.; Kawabata, T
    • Journal Title

      Chem, E. J

      Volume: 18 Pages: 15330-15336

    • DOI

      DOI:10.1002/chem.201201339

    • Peer Reviewed
  • [Presentation] β-脱離基を持つ C-N 軸性不斉エノラートの反応性:セリン誘導体を用いる β-ラクタムの不斉合成2012

    • Author(s)
      百武龍一,多久和正訓,楊畔,吉村智之,川端猛夫
    • Organizer
      第30回メディシナルケミストリーシンポジウム
    • Place of Presentation
      東京・タワーホール船堀
    • Year and Date
      2012-11-29
  • [Presentation] 不斉記憶型分子間共役付加反応の開発と manzacidin A の全合成2012

    • Author(s)
      木下智彦,吉岡広泰,吉村智之,川端猛夫
    • Organizer
      第102回有機合成シンポジウム
    • Place of Presentation
      早稲田大学国際会議場・東京
    • Year and Date
      2012-11-08
  • [Presentation] プロトン化によって促進される不斉記憶型分子内共役付加反応を活用した高歪み β-ラクタムの不斉合成2012

    • Author(s)
      吉村智之,多久和正訓,友原啓介,宇山允人,林一広,楊畔,百武龍一,川端猛夫
    • Organizer
      第62回日本薬学会近畿支部総会・大会
    • Place of Presentation
      西宮・武庫川女子大学
    • Year and Date
      2012-10-20
  • [Presentation] Intramolecular conjugate addition of axially chiral enolates possessing a β-alkoxy leaving group: Asymmetric synthesis of β-lactams from L-serine derivatives2012

    • Author(s)
      Ryuichi Hyakutake, Masatoshi Takuwa, Makoto Uyama, Tomoyuki Yoshimura, Takeo Kawabata
    • Organizer
      The 10th International Conference on Heteroatom Chemistry
    • Place of Presentation
      Obaku Plaza, Uji, Japan
    • Year and Date
      2012-05-22
  • [Presentation] Total Synthesis of Manzacidin A via Asymmetric Intermolecular Conjugate Addition Reaction Based on Memory of Chirality2012

    • Author(s)
      Tomohiko Kinoshita, Hiroyasu Yoshioka, Tomoyuki Yoshimura, Takeo Kawabata
    • Organizer
      Symposium on Molecular Chirality ASIA 2012
    • Place of Presentation
      Centennial Hall, Kyushu University School of Medicine
    • Year and Date
      2012-05-17
  • [Presentation] キラルエノラートの分子内共役付加を利用する多置換 β-ラクタムの不斉合成2011

    • Author(s)
      吉村智之,多久和正訓,楊畔,友原啓介 ,川端猛夫
    • Organizer
      第61回日本薬学会近畿支部総会・大会
    • Place of Presentation
      神戸学院大学
    • Year and Date
      2011-10-22
  • [Remarks]

    • URL

      http://www.fos.kuicr.kyoto-u.ac.jp/

URL: 

Published: 2014-09-25  

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