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Asymmetric syntheses of biologically active heterocyclic natural products employing catalytic C-H activation strategy

Research Project

Project/Area Number 24590001
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionUniversity of Toyama

Principal Investigator

NAMBU Hisanori  富山大学, 大学院医学薬学研究部(薬学), 准教授 (80399956)

Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2014: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2012: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Keywords複素環化合物 / C-H結合活性化 / 生物活性天然物 / C-H挿入反応 / 触媒反応 / ロジウム(II)錯体 / 不斉合成 / ジヒドロベンゾフラン / C-Hオレフィン化 / ロジウム(II)触媒 / ネオリグナン / スチルベンダイマー
Outline of Final Research Achievements

Asymmetric synthesis of (-)-trans-blechnic acid, a dihydrobenzofuran neolignan natural product, has been achieved by employing Rh(II)-catalyzed intramolecular C-H insertion reaction of aryldiazoacetate and Pd(II)-catalyzed intermolecular C-H olefination reaction as key steps.
Asymmetric synthesis of (-)-E-δ-viniferin, a trans-resveratrol dimer natural product containing a dihydrobenzofuran ring, has been achieved by exploiting Rh(II)-catalyzed intramolecular C-H insertion reaction of a diaryldiazomethane derivative as a key step.

Report

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

    (16 results)

All 2015 2014 2013 2012 Other

All Journal Article (6 results) (of which Peer Reviewed: 6 results,  Acknowledgement Compliant: 2 results) Presentation (5 results) (of which Invited: 1 results) Remarks (3 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Diastereo- and enantioselective intramolecular 1,6-C-H insertion reactions of α-diazo esters catalyzed by chiral dirhodium(II) carboxylates2015

    • Author(s)
      Ito, M.; Kondo, Y.; Nambu, H.; Anana, M.; Takeda, K.; Hashimoto, S.
    • Journal Title

      Tetrahedron Lett.

      Volume: 56 Issue: 11 Pages: 1397-1400

    • DOI

      10.1016/j.tetlet.2015.01.125

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Ring-Opening Cyclization of Cyclohexane-1,3-dione-2-spirocyclopropanes with Amines: Rapid Access to 2-Substituted 4-Hydroxyindole2014

    • Author(s)
      Nambu, H.; Fukumoto, M.; Hirota, W.; Yakura, T.
    • Journal Title

      Org. Lett.

      Volume: 16 Issue: 15 Pages: 4012-4015

    • DOI

      10.1021/ol501837b

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Asymmetric Total Synthesis of (-)-trans-Blechnic Acid via Rhodium(II)-Catalyzed C-H Insertion and Palladium(II)-Catalyzed C-H Olefination Reactions2014

    • Author(s)
      Ito, M.; Namie, R; Krishnamurthi, J.; Miyamae, H.; Takeda, K.; Nambu, H.; Hashimoto, S.*
    • Journal Title

      Synlett

      Volume: 25 Issue: 02 Pages: 288-292

    • DOI

      10.1055/s-0033-1340291

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] A 2-Iodobenzamide Catalyst for Oxidation of Alcohols at Room Temperature2014

    • Author(s)
      Yakura, T.; Yamada, A.; Noda, N,; Fujiwara, T.; Nambu, H.
    • Journal Title

      Asian. J. Org. Chem.

      Volume: 3 Issue: 4 Pages: 421-424

    • DOI

      10.1002/ajoc.201300279

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] A Polymer-Supported Chiral Fluorinated Dirhodium(II) Complex for Asymmetric Amination of Silyl Enol Ethers2012

    • Author(s)
      Oohara, T.
    • Journal Title

      Adv. Synth. Catal.

      Volume: 354 Issue: 11-12 Pages: 2331-2338

    • DOI

      10.1002/adsc.201200219

    • URL

      http://dx.doi.org/

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] A Stereocontrolled Construction of 2-Azido-2-deoxy-1,2-cis-α-galactosidic Linkages Utilizing 2- Azido-4,6-O-benzylidene-2-deoxygalactopyranosyl Diphenyl Phosphates: Stereoselective Synthesis of Mucin Core 5 and Core 7 Structures2012

    • Author(s)
      Kakita, K.
    • Journal Title

      Tetrahedron

      Volume: 68 Issue: 25 Pages: 5005-5017

    • DOI

      10.1016/j.tet.2012.04.059

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] アミンによる位置選択的シクロプロパン開裂反応を用いる多置換インドール類の新規合成法の開発2014

    • Author(s)
      南部寿則,廣田 渉,福本昌紘,矢倉隆之
    • Organizer
      平成26年度有機合成化学北陸セミナー
    • Place of Presentation
      港のホテル(福井県坂井市)
    • Year and Date
      2014-10-03 – 2014-10-04
    • Related Report
      2014 Annual Research Report
  • [Presentation] アミンによるシクロプロパンの開裂に続く環形成反応を用いるインドールの合成2014

    • Author(s)
      南部寿則,福本昌紘,廣田 渉,矢倉隆之
    • Organizer
      第44回複素環化学討論会
    • Place of Presentation
      札幌市民ホール(札幌市中央区)
    • Year and Date
      2014-09-10 – 2014-09-12
    • Related Report
      2014 Annual Research Report
  • [Presentation] 不斉C-H挿入とC-Hオレフィン化を基盤とする(-)-ブレクニン酸の全合成2013

    • Author(s)
      浪江亮介, 宮前 瞳, 伊藤元気, 南部寿則, 橋本俊一
    • Organizer
      第39回反応と合成の進歩シンポジウム
    • Place of Presentation
      福岡
    • Related Report
      2013 Research-status Report
  • [Presentation] グリコシルジフェニルホスファートを用いる1,2-cis-α-グリコシド結合の立体選択的構築とその応用2012

    • Author(s)
      南部寿則
    • Organizer
      平成24年度有機合成化学北陸セミナー
    • Place of Presentation
      富山
    • Related Report
      2012 Research-status Report
  • [Presentation] キラルなロジウム(II)錯体を用いた触媒的不斉合成反応

    • Author(s)
      南部寿則
    • Organizer
      創薬基盤化学研究若手セミナー(立命館大学創薬科学研究センター)
    • Place of Presentation
      滋賀
    • Related Report
      2012 Research-status Report
    • Invited
  • [Remarks] 薬品製造化学研究室ホームページ

    • URL

      http://www.pharm.hokudai.ac.jp/yakuzou/hashimotolab/index.html

    • Related Report
      2014 Annual Research Report
  • [Remarks] 薬品製造化学研究室

    • URL

      http://www.pharm.hokudai.ac.jp/yakuzou/index.html

    • Related Report
      2013 Research-status Report
  • [Remarks] 薬品製造化学研究室

    • URL

      http://www.pharm.hokudai.ac.jp/yakuzou/index.html

    • Related Report
      2012 Research-status Report
  • [Patent(Industrial Property Rights)] ヨードベンズアミド型アルコール酸化触媒2014

    • Inventor(s)
      矢倉隆之,南部寿則,藤原朋也,野田成美,山田明広
    • Industrial Property Rights Holder
      矢倉隆之,南部寿則,藤原朋也,野田成美,山田明広
    • Industrial Property Rights Type
      特許
    • Filing Date
      2014-03-12
    • Related Report
      2013 Research-status Report
  • [Patent(Industrial Property Rights)] 磁性鉄粒子担持ヨウ素触媒2014

    • Inventor(s)
      矢倉隆之,南部寿則,藤原朋也
    • Industrial Property Rights Holder
      矢倉隆之,南部寿則,藤原朋也
    • Industrial Property Rights Type
      特許
    • Filing Date
      2014-03-25
    • Related Report
      2013 Research-status Report

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

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