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Development of New Allylation reagent and Its aplication for straightforward organic synthesis

Research Project

Project/Area Number 24550125
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionOkayama University of Science

Principal Investigator

NOKAMI Junzo  岡山理科大学, 工学部, 教授 (70109742)

Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000)
Fiscal Year 2014: ¥520,000 (Direct Cost: ¥400,000、Indirect Cost: ¥120,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2012: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
KeywordsAllyl-Transfer 反応 / 不斉アリル化 / 炭素アリル化剤 / 直截的有機合成 / 酸触媒 / YH AE (山本尚不斉エポキシ化) / 光学活性ホモアリルアルコール / YH AE / allyl-transfer 反応 / Nokami alcohol
Outline of Final Research Achievements

As the allylation of aldehydes via Allyl-Transfer reaction takes place by stable carbon allyl donors without using unstable organometallic allylic reagents, not only chiral allyl donors for asymmetric synthesis but also functionalized chiral allyl donors for straightforward synthesis of useful organic compounds such as bioactive natural compounds are available. Preparation of an optically active homoallylic alcohol is essential to obtain a chiral carbon allyl donor. We discovered that chiral allyl donors were available via Yamamoto's catalytic asymmetric epoxidation of homoallylic alcohols, although traditional method such as Sharpless AE did not give a satisfactory result. Now, straightforward synthesis of useful compounds is in progress by using newly prepared carbon allyl donors.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (21 results)

All 2015 2014 2013 2012

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (15 results)

  • [Journal Article] Synthetic Access to Poly-Substituted 11H-Pyrido[3,2-a]Carbazoles, A DNA-Intercalating Ellipticine Related Structure, and Their Antiproliferative Activity2014

    • Author(s)
      Ming-Yu Wu, Elkhabiry Shaban, Marta Switalska, Ning Wang, Miho Shimoda, Yusuke Mizutani, Megumi Yoshida, Zhen-Wu Mei, Hiroyuki Kawafuchi, Junzo Nokami, Joanna Wietrzyk, Xiao-Qi Yu, Tsutomu Inokuchi
    • Journal Title

      Heterocycles

      Volume: 89 Pages: 1427-1440

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Design, Synthesis, and Biological Evaluation of Artemisinin-Indoloquinoline Hybrids as Potent Antiproliferative Agents2014

    • Author(s)
      Li Wang, Marta Switalska, Ning Wang, Zhen-Jun Du, Yuta Fukumoto, Nguyen Kim Diep, Ryo Kiguchi, Junzo Nokami, Joanna Wietrzyk, Tsutomu Inokuchi
    • Journal Title

      Molecules

      Volume: 19 Pages: 19021-19035

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthetic Access to Poly-substituted 11H-Pyrido[3,2-a]carbazoles, A DNA-intercalating Ellipticine Related Struccture, and Their Antiproliferative Activity2014

    • Author(s)
      Ming-Yu Wu, Elkhabiry Shaban, Marta Switalska, Ning Wang, Miho Shimoda, Yusuke Mizutani, Megumi Yoshida, Zhen-Wu Mei, Hiroyuki Kawafuchi, Junzo Nokami, Joanna Wietrzyk, Xiao-Qi Yu, Tsutomu Inokuchi
    • Journal Title

      Heterocycles

      Volume: 89

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Cyclopentanoids from Cyclopentadiene: Synthesis of (-)-Methyl Jasmonate and (+)-12-Oxophytodienoic acid2013

    • Author(s)
      Junzo Nokami, Kazuhiko Fujii, Yusuke Mizutani, Rikiya Omatsu, Kiyoshi Watanabe, Hiroshi Yasuda, Tsutomu Inokuchi
    • Journal Title

      Natural Product Communication

      Volume: 8 Pages: 919-923

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Regioselective N-Methylation of 6-Chloroindole[3,2-c]quinolines and Their Amination Reactivity at the C-6 Position2013

    • Author(s)
      Ning Wang, Kento Imai, Cui-Qing Pang, Ming-qi Wang, Mizuho Yonezawa, Yu Zhang, Junzo Nokami, Tsutomu Inokuchi
    • Journal Title

      Bull. Chem. Soc. Jpn

      Volume: 86 Pages: 864-869

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Cyclopentanoids from Cyclopentadiene: Synthesis of (-)-methyl jasmonate and (+)-12-oxophytodienoic acid2013

    • Author(s)
      Junzo Nokami, Kazuhiko Fujii, Yusuke Mizutani, Rikiya Omatsu, Kiyoshi Watanabe, Hiroshi Yasuda, Tsutomu Inokuchi
    • Journal Title

      Natural Product Communications

      Volume: 7 Pages: 1-5

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] Allyl-Transfer reaction resolves the chemistry of allylation of aldehyde2015

    • Author(s)
      NOKAMI, Junzo; ANDO, Maimi; YAMAZAKI, Shigeo
    • Organizer
      日本化学会 第95春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] 酵素による光学活性ビルディングブロック調製とそれを用いる光学活性テルペノイド合成2014

    • Author(s)
      野上潤造○安藤舞美・王 寧・井口 勉・山崎重雄
    • Organizer
      第58回香料・テルペンおよび精油化学に関する討論会
    • Place of Presentation
      和歌山
    • Year and Date
      2014-09-20 – 2014-09-22
    • Related Report
      2014 Annual Research Report
  • [Presentation] 酵素反応によって調製したビルディングブロックを用いる光学活性天然物の合成2014

    • Author(s)
      安藤 舞美・王 寧・野上 潤造・井口 勉・山崎 重雄
    • Organizer
      第8 回バイオ関連化学プログラム(日本化学会)
    • Place of Presentation
      岡山
    • Year and Date
      2014-09-11 – 2014-09-12
    • Related Report
      2014 Annual Research Report
  • [Presentation] 16員環マクロライド (-)-A26771B の簡便全合成2014

    • Author(s)
      野上潤造・水谷祐介・王 寧・井口 勉
    • Organizer
      日本化学会第94回春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] Sulfinyl-Knoevenagel 反応を用いた(-)-A26771B 合成2013

    • Author(s)
      水谷祐介, 野上潤造
    • Organizer
      57th 香料・テルペンおよび精油化学に関する討論会
    • Place of Presentation
      埼玉大学
    • Related Report
      2013 Research-status Report
  • [Presentation] Sulfinyl-Knoevenagel 反応を用いるethyl 4-hydroxyalk-2-enoate の簡便合成と大環 状ラクトン (-)-A26771B 合成への応用2013

    • Author(s)
      水谷祐介, 藤井康貴 横山円香 野上潤造
    • Organizer
      日本化学会第93回春季年会
    • Place of Presentation
      立命館大学草津キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] 酵素反応による光学活性 building block の調製とこれを用いる光学活性天然物の 全合成2013

    • Author(s)
      水谷祐介, 野上潤造
    • Organizer
      第17回生体触媒化学シンポジウム
    • Place of Presentation
      岡山理科大学
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis of Optically Active Natural Products using Chiral Building Blocks Prepared by Enzymatic Reaction2013

    • Author(s)
      Yusuke Mizutani, Junzo Nokami
    • Organizer
      1st European Conference on Natural Products (ECNP-1)
    • Place of Presentation
      Frankfurt (Dechema)
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis of (-)-A26771B via Sulfinyl-Knoevenagel Reaction of Aldehydes with Ethyl 2-(2-benzothiazolylsulfinyl) acetate2013

    • Author(s)
      Yusuke Mizutani, Zhenjun Du, and Junzo Nokami
    • Organizer
      The International Symposium on Organic Reaction (ISOR-11)
    • Place of Presentation
      Taipei
    • Related Report
      2013 Research-status Report
  • [Presentation] Oxidation of Sulfide to Sulfoxide and Its Application for Synthesis of Bioactive Natural Prpducts2013

    • Author(s)
      Yusuke Mizutani, Ning Wang, Tsutomu Inokuchi, and Junzo Nokami
    • Organizer
      The 4th German-Japanese Symposium on Electrosynthesis (GJSE-4)
    • Place of Presentation
      Kyoto (京大桂)
    • Related Report
      2013 Research-status Report
  • [Presentation] Allyl-Transfer 反応を用いるアルデヒドの不斉アリル化―アルデヒドの反応性―2013

    • Author(s)
      廣田大地・藤井一彦・水谷祐介・野上潤造
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津(滋賀県)
    • Related Report
      2012 Research-status Report
  • [Presentation] Sulfinyl-Knoevenagel反応を用いるethyl 4-hydroxyalk-2-enoateの簡便合成と大環状ラクトンA26771B合成への応用2013

    • Author(s)
      水谷祐介・藤井康貴・横山円香・野上潤造
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津(滋賀県)
    • Related Report
      2012 Research-status Report
  • [Presentation] Stereoselective Allylation of Aldehydes using Nonmetallic Allyl Donors2012

    • Author(s)
      Junzo Nokami, Kazuhiko Fujii, Daichi Hirota, Yusuke Fujino, Daiki Nishigaki
    • Organizer
      The 12th International Kyoto conference on New Aspects of Organic Chemistry
    • Place of Presentation
      Kyoto
    • Related Report
      2012 Research-status Report
  • [Presentation] 光学活性テルペンを不斉補助基とする炭素アリル化剤によるアルデヒドの不斉アリル化2012

    • Author(s)
      西垣大輝・廣田大地・加賀裕行・野上潤造
    • Organizer
      第56回香料・テルペンおよび精油化学に関する討論会
    • Place of Presentation
      鹿児島
    • Related Report
      2012 Research-status Report
  • [Presentation] 光学活性γ-ヒドロキシ-α,β-不飽和エステルの簡便合成2012

    • Author(s)
      水谷祐介・藤井康貴・横山円香・野上潤造
    • Organizer
      第56回香料・テルペンおよび精油化学に関する討論会
    • Place of Presentation
      鹿児島
    • Related Report
      2012 Research-status Report

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Published: 2013-05-31   Modified: 2019-07-29  

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