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Development of antioxidant with lignan skeleton

Research Project

Project/Area Number 21590032
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionOsaka Ohtani University

Principal Investigator

MAEZAKI Naoyoshi  大阪大谷大学, 薬学部, 教授 (00229296)

Co-Investigator(Renkei-kenkyūsha) HIROKAWA Yoshimi  大阪大谷大学, 薬学部, 准教授 (40454582)
KITAMURA Maria  大阪大谷大学, 薬学部, 助教 (00434811)
Project Period (FY) 2009 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000)
Fiscal Year 2011: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2010: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2009: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Keywords抗酸化剤 / リグナン / 有機化学 / 不斉合成 / [2, 3]-Wittig転位反応 / [2,3]-Wittig転位反応
Research Abstract

We have investigated a syntheses of eupomatilones and tetrahydrofuran lignans to develop antioxidant with lignan skeleton. As a result, we have achieved a total synthesis of eupomatilones 1, 2, and 5 using asymmetric [2, 3]-Wittig rearrangement as a key reaction with high enantioselectivities(88.91% ee). We also succeeded to synthesize stereoisomers of THF-lignan.

Report

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

    (28 results)

All 2012 2011 2010 2009 Other

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (22 results)

  • [Journal Article] Bis(oxazoline)-ligand-mediated asymmetric[2, 3]-Wittig rearrangement of benzyl ethers : Reaction mechanism based on the hydrogen/deuterium exchange effect2012

    • Author(s)
      M. Kitamura, Y. Hirokawa, Y. Yoshioka, and N. Maezaki
    • Journal Title

      Tetrahedron

      Volume: 68(22) Issue: 22 Pages: 4280-4285

    • DOI

      10.1016/j.tet.2012.03.059

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of(+)-Eupomatilone 2 via Asymmetric[2, 3]-Wittig Rearrangement of Highly Oxygenated Biphenylmethyl Ethers2011

    • Author(s)
      Y. Hirokawa, M. Kitamura, C. Kato, Y. Kurata, and N. Maezaki
    • Journal Title

      Tetrahedron Lett

      Volume: 52(5) Issue: 5 Pages: 581-583

    • DOI

      10.1016/j.tetlet.2010.11.126

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of(+)-Eupomatilone 2 via Asymmetric [2,3]-Wittig Rearrangement of Highly Oxygenated Biphenylmethyl Ethers2011

    • Author(s)
      HIROKAWA, Yoshimi
    • Journal Title

      Tetrahedron Letters

      Volume: 52・5 Pages: 581-583

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric [2, 3]-Wittig Rearrangement of Oxygenated Allyl Benzyl Ethers in the Presence of a Chiral di-tBu-bis(oxazoline) Ligand : A Novel Synthetic Approach to THF Lignans2009

    • Author(s)
      M. Kitamura, Y. Hirokawa, and N. Maezaki
    • Journal Title

      Chem. Eur. J

      Volume: 15(38) Issue: 38 Pages: 9911-9917

    • DOI

      10.1002/chem.200901212

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric [2,3]-Wittig Rearrangement of Oxygenated Allyl Benzyl Ethers in the Presence of a Chiral di-tBu-bis(oxazoline) Ligand : A Novel Synthetic Approach to THE Lignans2009

    • Author(s)
      KITAMURA, Maria
    • Journal Title

      Chemistry-A European Journal 15・38

      Pages: 9911-9917

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Bis(oxazoline)-ligand-mediated asymmetric [2,3]-Wittig rearrangement of benzyl ethers : Reaction mechanism based on the hydrogen/deuterium exchange effect

    • Author(s)
      KITAMURA, Maria
    • Journal Title

      Tetrahedron, 2012

      Volume: (in press)

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Presentation] 不斉[2, 3]-Wittig転位反応を鍵反応としたeupomatilone類の不斉合成研究2012

    • Author(s)
      水林誠, 北村麻理愛, 広川美視, 加藤千晴, 倉田祐希, 前崎直容
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      北海道
    • Year and Date
      2012-03-29
    • Related Report
      2011 Final Research Report
  • [Presentation] 不斉[2,3]-Wittig転位反応を鍵反応としたeupomatilone類の不斉合成研究2012

    • Author(s)
      水林誠
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      北海道大学(北海道)
    • Year and Date
      2012-03-29
    • Related Report
      2011 Annual Research Report
  • [Presentation] A Synthesis of Eupomatilones Using Enantioselective [2, 3]-Wittig Rearrangement2011

    • Author(s)
      M. Kitamura, Y. Hirokawa, C. Kato, Y. Kurata, M. Mizubayashi, and N. Maezaki
    • Organizer
      8th AFMC International Medicinal Chemistry Symposium Frontier of Medicinal Science
    • Place of Presentation
      東京
    • Year and Date
      2011-11-30
    • Related Report
      2011 Final Research Report
  • [Presentation] A Synthesis of Eupomatilones Using Enantioselective [2,3]-Wittig Rearrangement2011

    • Author(s)
      北村麻理愛
    • Organizer
      8th AFMC International Medicinal Chemistry Symposium Frontier of Medicinal Science AIMECS11(2011)
    • Place of Presentation
      京王プラザホテル(東京)
    • Year and Date
      2011-11-30
    • Related Report
      2011 Annual Research Report
  • [Presentation] 光学活性ビスオキサゾリン配位子を用いたベンジルエーテル類の不斉[2, 3]-Wittig転位反応の反応機構の考察2011

    • Author(s)
      北村麻理愛, 吉岡勇輝, 広川美視, 前崎直容
    • Organizer
      第37回反応と合成の進歩シンポジウム
    • Place of Presentation
      徳島
    • Year and Date
      2011-11-08
    • Related Report
      2011 Final Research Report
  • [Presentation] 光学活性ビスオキサゾリン配位子を用いたベンジルエーテル類の不斉[2,3]-Wittig転位反応の反応機構の考察2011

    • Author(s)
      北村麻理愛
    • Organizer
      第37回反応と合成の進歩シンポジウム
    • Place of Presentation
      あわぎんホール(徳島)
    • Year and Date
      2011-11-08
    • Related Report
      2011 Annual Research Report
  • [Presentation] Eupomatilone類縁体の合成研究2011

    • Author(s)
      北村麻理愛, 広川美視, 前崎直容
    • Organizer
      第41回複素環化学討論会
    • Place of Presentation
      熊本
    • Year and Date
      2011-10-20
    • Related Report
      2011 Final Research Report
  • [Presentation] Eupomatilone類縁体の合成研究2011

    • Author(s)
      北村麻理愛
    • Organizer
      第41回複素環化学討論会
    • Place of Presentation
      崇城大学市民ホール(熊本)
    • Year and Date
      2011-10-20
    • Related Report
      2011 Annual Research Report
  • [Presentation] 2, 5-ジアリールTHFリグナンの各種立体異性体の合成研究2011

    • Author(s)
      守行美穂, 北村麻理愛, 広川美視, 前崎直容
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-31
    • Related Report
      2011 Final Research Report
  • [Presentation] Eupomatilone 2及びその類縁体の不斉合成2011

    • Author(s)
      加藤千晴, 倉田祐希, 広川美視, 北村麻理愛, 前崎直容
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-31
    • Related Report
      2011 Final Research Report
  • [Presentation] Eupomatilone 2の不斉合成研究2010

    • Author(s)
      北村麻理愛, 加藤千晴, 倉田祐樹, 広川美視, 前崎直容
    • Organizer
      第60回日本薬学会近畿支部大会
    • Place of Presentation
      大阪
    • Year and Date
      2010-10-30
    • Related Report
      2011 Final Research Report
  • [Presentation] Eupomatilone 2の不斉合成研究2010

    • Author(s)
      北村麻理愛
    • Organizer
      第60回日本薬学会近畿支部大会
    • Place of Presentation
      摂南大学(大阪)
    • Year and Date
      2010-10-30
    • Related Report
      2010 Annual Research Report
  • [Presentation] Eupomatilone 2の合成2010

    • Author(s)
      前崎直容, 加藤千晴, 倉田祐樹, 北村麻理愛, 広川美視
    • Organizer
      第40回複素環化学討論会
    • Place of Presentation
      仙台
    • Year and Date
      2010-10-14
    • Related Report
      2011 Final Research Report
  • [Presentation] Eupomatilone 2の合成2010

    • Author(s)
      前崎直容
    • Organizer
      第40回複素環化学討論会
    • Place of Presentation
      仙台市民会館(仙台)
    • Year and Date
      2010-10-14
    • Related Report
      2010 Annual Research Report
  • [Presentation] 2,5-ジアリールTHFリグナンの各種立体異性体の合成研究2010

    • Author(s)
      守行美穂
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡コンベンションアーツセンター(静岡)
    • Year and Date
      2010-03-31
    • Related Report
      2010 Annual Research Report
  • [Presentation] 不斉[2, 3]-Wittig転位反応を鍵反応としたTHF-リグナン類の合成法の研究2010

    • Author(s)
      広川美視, 北村麻理愛, 前崎直容
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-28
    • Related Report
      2011 Final Research Report
  • [Presentation] 不斉[2,3]-Wittig転位反応を鍵反応としたTHF-リグナン類の合成法の研究2010

    • Author(s)
      広川美視, 北村麻理愛, 前崎直容
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      桃太郎アリーナ(岡山)
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] 不斉[2, 3]-Wittig転位反応を鍵反応としたリグナン類の系統的合成研究2009

    • Author(s)
      北村麻理愛, 広川美視, 前崎直容
    • Organizer
      第59回日本薬学会近畿支部大会
    • Place of Presentation
      大阪
    • Year and Date
      2009-10-24
    • Related Report
      2011 Final Research Report
  • [Presentation] 不斉[2,3]-Wittig転位反応を鍵反応としたリグナン類の系統的合成研究2009

    • Author(s)
      北村麻理愛, 広川美視, 前崎直容
    • Organizer
      第59回日本薬学会近畿支部大会
    • Place of Presentation
      近畿大学(大阪)
    • Year and Date
      2009-10-24
    • Related Report
      2009 Annual Research Report
  • [Presentation] ベンジルエーテル類の不斉[2, 3]-Wittig転位反応-反応機構の考察-2009

    • Author(s)
      前崎直容, 北村麻理愛, 広川美視
    • Organizer
      第39回複素環化学討論会
    • Place of Presentation
      千葉
    • Year and Date
      2009-10-15
    • Related Report
      2011 Final Research Report
  • [Presentation] ベンジルエーテル類の不斉[2,3]-Wittig転位反応-反応機構の考察-2009

    • Author(s)
      前崎直容, 北村麻理愛, 広川美視
    • Organizer
      第22回複素環化学討論会
    • Place of Presentation
      さわやかちば県民プラザ(千葉)
    • Year and Date
      2009-10-15
    • Related Report
      2009 Annual Research Report
  • [Presentation] Application Of Enantioselective [2, 3]-Wittig Rearrangement To Construction Of Lignan Skeleton2009

    • Author(s)
      北村麻理愛, 広川美視, 前崎直容
    • Organizer
      第22回国際複素環化学会議
    • Place of Presentation
      セント・ジョーンズ,カナダ
    • Year and Date
      2009-08-05
    • Related Report
      2011 Final Research Report

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

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