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Study of asymmetric total synthesis of nakadomarin A

Research Project

Project/Area Number 21790012
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionKanazawa University

Principal Investigator

INAGAKI Fuyuhiko  Kanazawa University, 薬学系, 助教 (80506816)

Project Period (FY) 2009 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2010: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2009: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Keywords有機化学 / ナカドマリンA / Pauson-Khand 反応 / 天然物合成 / アレン / Pauson-Khand / Pauson-Khand反応
Research Abstract

We completed the total synthesis of (+)-nakadomarin in a highly stereoselectve manner from the commercially available L-pyroglutamic acid. The most significant point of this synthesis involves the intramolecular Pauson-Khand reaction between the alkyne and N-protected-dihydropyrrole functionalities, which enabled us to construct the diazatricyclo[6.4.0.0^<1,5>]dodcadienone product. This reaction was also useful for the short-step synthesis of (±)-meloscine. In addition, we succeeded to extend the application of the rhodium catalyzed Pauson-Khand type reaction of allenenes for the construction of bicyclo[4.3.0] skeletons containing quaternary carbon at the ring juncture. This method provided a new procedure for the construction of the tricyclo[6.4.0.0^<1,5>]dodecenone framework in a satisfactory yield.

Report

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

    (38 results)

All 2011 2010 2009

All Journal Article (16 results) (of which Peer Reviewed: 16 results) Presentation (22 results)

  • [Journal Article] Org.2011

    • Author(s)
      Inagaki, F., Itoh, N., Hayashi, Y.,Matsui, Y., Mukai, C.,Beilstein J.
    • Journal Title

      Chem. 7

      Pages: 404-409

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Org.2011

    • Author(s)
      Hayashi, Y., Inagaki, F., Mukai, C.
    • Journal Title

      Lett 13

      Pages: 1778-1780

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article]2011

    • Author(s)
      Inagaki, F., Kitagaki, S., Mukai, C.
    • Journal Title

      Synlett

      Pages: 594-614

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Rh(1)-catalyzed Intramolecular [2+2+1] Cycloaddition of Allenenes : Construction of Ricyclo[4.3.0]nonenones with an Angular Methyl Group and Tricyclo[6.4.0.0^<1.5>]dodecenone2011

    • Author(s)
      F.Inagaki
    • Journal Title

      Beilstein J.Org.Chem.

      Volume: 7 Pages: 404-409

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of (±)-Meloscine2011

    • Author(s)
      Y.Hayashi
    • Journal Title

      Org.Lett.

      Volume: 13 Pages: 1778-1780

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Construction of Diverse Ring Systems Based on Allene-Multiple Bond Cycloaddition2011

    • Author(s)
      F.Inagaki
    • Journal Title

      Synlett

      Pages: 594-614

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chem.2010

    • Author(s)
      Kawamura, T., Inagaki, F., Narita, S.,Takahashi, Y., Hirata, S., Kitagaki, S.,Mukai, C.
    • Journal Title

      Eur.J. 16

      Pages: 5173-5183

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Org.2010

    • Author(s)
      Inagaki, F., Kinebuchi, M., Miyakoshi,N., Mukai, C.
    • Journal Title

      Lett 12

      Pages: 1800-1803

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Angew.Chem.2010

    • Author(s)
      Inagaki, F., Sugikubo, K., Miyashita,Y., Mukai, C.
    • Journal Title

      Int.Ed. 49

      Pages: 2206-2210

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium(I)-Catalyzed Intramolecular Carbonylative [2+2+1]Cycloadditions and Cycloisomerizations of Bis(sulfonylallene)s2010

    • Author(s)
      T.Kawamura
    • Journal Title

      Chem.Eur.J.

      Volume: 16 Pages: 5173-5183

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Formal Synthesis of (+)-Nakadomarin A2010

    • Author(s)
      Inagaki, F.
    • Journal Title

      Org.Lett. (in press)

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium(I)-Catalyzed Intramolecular [5+2] Cycloaddition Reactions of Alkynes and Allenylc yclopropanes : Construction of Bicyclo[5.4.0]undecatrienes and Bicyclo[5.4.0]dodecatrienes2010

    • Author(s)
      Inagaki, F
    • Journal Title

      Angew.Chem.Int.Ed. 49

      Pages: 2206-2210

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] J.Org.2009

    • Author(s)
      Aburano, D., Inagaki, F., Tomonaga, S.,Mukai, C.
    • Journal Title

      Chem 74

      Pages: 5590-5594

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] J.Org.2009

    • Author(s)
      Inagaki, F., Mizutani, M., Kuroda, N.,Mukai, C.
    • Journal Title

      Chem. 74

      Pages: 6402-6405

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of a Core Carbon Framework of Cyanosporasides A and B2009

    • Author(s)
      Aburano, D
    • Journal Title

      J.Org.Chem. 74

      Pages: 5590-5594

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Generation of N-(tert-Butoxycarbonyl)indole-2, 3-quinodimethane and Its [4+2]-Type Cycloaddition2009

    • Author(s)
      Inagaki, F
    • Journal Title

      J.Org.Chem. 74

      Pages: 6402-6405

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Presentation] ニトロンとスルホニルアレンとの位置選択的分子内[3+2]環化付加反応2011

    • Author(s)
      稲垣冬彦, 小林春美, 向智里
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      東日本大震災のため誌上開催
    • Year and Date
      2011-03-31
    • Related Report
      2010 Final Research Report
  • [Presentation] Diels-Alder反応を利用したビシクロ[m.4.0]骨格(m=6,7)の効率的構築法の開発2011

    • Author(s)
      稲垣冬彦, 高橋康仁, 向智里
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      東日本大震災のため誌上開催
    • Year and Date
      2011-03-31
    • Related Report
      2010 Final Research Report
  • [Presentation] (±)-Scandineの合成研究2011

    • Author(s)
      林佑次郎
    • Organizer
      日本薬学会 第131年会
    • Place of Presentation
      (東日本大震災のため誌上開催)
    • Year and Date
      2011-03-29
    • Related Report
      2010 Annual Research Report
  • [Presentation] 多重結合の特性を活用した分子内環化反応とその応用2010

    • Author(s)
      稲垣冬彦
    • Organizer
      日本薬学会北陸支部第122回例会
    • Place of Presentation
      北陸大学(石川県)
    • Year and Date
      2010-11-21
    • Related Report
      2010 Final Research Report
  • [Presentation] 多置換型ビスアレンを用いたRh(I)触媒分子内Pauson-Khand型反応の開発2010

    • Author(s)
      稲垣冬彦, 高橋康仁, 小川久美子, 成田集, 向智里
    • Organizer
      日本薬学会北陸支部第122回例会
    • Place of Presentation
      北陸大学(石川県)
    • Year and Date
      2010-11-21
    • Related Report
      2010 Final Research Report
  • [Presentation] 多重結合の特性な活用した分子内環化反応とその応用2010

    • Author(s)
      稲垣冬彦
    • Organizer
      日本薬学会北陸支部第122回例会
    • Place of Presentation
      北陸大学アネックスファーム(石川県)(招待講演)
    • Year and Date
      2010-11-21
    • Related Report
      2010 Annual Research Report
  • [Presentation] アレンを基盤とする中員環含有双環性骨格の新規構築2010

    • Author(s)
      稲垣冬彦, 川村行正, 杉窪克哉, 成田集,宮下祐輔, 平田修一, 北垣伸治, 向智里
    • Organizer
      第36回反応と合成の進歩シンポジウム-ライフサイエンスを志向した理論、反応および合成-
    • Place of Presentation
      ウインクあいち(愛知県)
    • Year and Date
      2010-11-01
    • Related Report
      2010 Final Research Report
  • [Presentation] アレンを基盤とする中員環含有双環性骨格の新規構築2010

    • Author(s)
      稲垣冬彦
    • Organizer
      反応と合成の進歩シンポジウム
    • Place of Presentation
      ウインクあいち(愛知県)
    • Year and Date
      2010-11-01
    • Related Report
      2010 Annual Research Report
  • [Presentation] Goniomitineの不斉全合成研究2010

    • Author(s)
      水谷仁弥, 稲垣冬彦, 向智里
    • Organizer
      第40回複素環化学討論会
    • Place of Presentation
      仙台市民会館(宮城県)
    • Year and Date
      2010-10-15
    • Related Report
      2010 Final Research Report
  • [Presentation] Pauson-Khand反応を活用した効率的な多環状天然物の合成:(±)-meloscine 及び(+)-nakadomarin A の全合成2010

    • Author(s)
      稲垣冬彦, 林佑次郎, 杵渕政彦, 宮腰直樹, 向智里
    • Organizer
      第8回次世代を担う有機化学シンポジウム
    • Place of Presentation
      日本薬学会長井記念ホール(東京都)
    • Year and Date
      2010-05-14
    • Related Report
      2010 Final Research Report
  • [Presentation] Pauson-Khand反応を活用した効率的な多環状天然物の合成:(+)-ナカドマリンA及びメロシンの全合成2010

    • Author(s)
      稲垣冬彦
    • Organizer
      第8回次世代な担う有機化学シンポジウム
    • Place of Presentation
      長井記念ホール(東京都)
    • Year and Date
      2010-05-14
    • Related Report
      2010 Annual Research Report
  • [Presentation] 2位置換アザインドール合成法の開発2010

    • Author(s)
      稲垣冬彦, Montaser Ahmed SHAYKOON,向智里
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山大学(岡山県)
    • Year and Date
      2010-03-30
    • Related Report
      2010 Final Research Report
  • [Presentation] Rh(I)触媒を活用したアルキン-アレニルシクロプロパンの[5+2]環化付加反応2010

    • Author(s)
      稲垣冬彦, 杉窪克哉, 宮下祐輔, 向智里
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山大学(岡山県)
    • Year and Date
      2010-03-30
    • Related Report
      2010 Final Research Report
  • [Presentation] Stereoselective Total Syntheses of fiveLycopodium Alkaloids Based onPauson-Khand Reaction2010

    • Author(s)
      Yasunari Otsuka, Takashi Kozaka,Fuyuhiko Inagaki, Chisato Mukai
    • Organizer
      金沢大学薬学系 北京大学葯学院 国際学術交流協定に基づく合同セミナー2010
    • Place of Presentation
      石川県広坂庁舎(石川県)
    • Year and Date
      2010-03-12
    • Related Report
      2010 Final Research Report
  • [Presentation] Pauson-Khand反応を活用した効率的な多環状天然物の合成; (+)-ナカドマリンA及びメロシンの全合成2010

    • Author(s)
      稲垣冬彦
    • Organizer
      金沢大学薬学シンポジウム
    • Place of Presentation
      金沢大学(石川県)
    • Year and Date
      2010-01-12
    • Related Report
      2010 Final Research Report
  • [Presentation] Pauson-Khand反応を活用した効率的な多環状天然物の合成;(+)-ナカドマリンA及びメロシンの全合成2010

    • Author(s)
      稲垣冬彦
    • Organizer
      金沢大学薬学シンポジウム
    • Place of Presentation
      金沢大学(石川県)
    • Year and Date
      2010-01-12
    • Related Report
      2009 Annual Research Report
  • [Presentation] Total Stntheses of Nakadomarin A and Meloscine Based on Pauson-Khand Reaction2009

    • Author(s)
      Mukai, C
    • Organizer
      Catalysis and Fine Chemicals 2009
    • Place of Presentation
      Korea University (Korea)
    • Year and Date
      2009-12-16
    • Related Report
      2009 Annual Research Report
  • [Presentation] Fawcettimineの全合成2009

    • Author(s)
      大塚安成, 稲垣冬彦, 向智里
    • Organizer
      第35回反応と合成の進歩シンポジウム-ライフサイエンスを志向した理論、反応および合成-
    • Place of Presentation
      金沢市文化ホール(石川県)
    • Year and Date
      2009-11-16
    • Related Report
      2010 Final Research Report
  • [Presentation] (±)-Meloscineの全合成研究2009

    • Author(s)
      林佑次郎, 稲垣冬彦, 松井祐美, 向智里
    • Organizer
      第39回複素環化学討論会
    • Place of Presentation
      さわやか千葉県民プラザ(千葉県)
    • Year and Date
      2009-10-14
    • Related Report
      2010 Final Research Report
  • [Presentation] (+)-ナカドマリンAの形式全合成2009

    • Author(s)
      稲垣冬彦
    • Organizer
      平成21年度有機合成化学北陸セミナー
    • Place of Presentation
      富山観光ホテル(富山県)
    • Year and Date
      2009-10-09
    • Related Report
      2009 Annual Research Report
  • [Presentation] C.Synthe ticstudies on (+)-nakadomarin A2009

    • Author(s)
      Inagaki, F.; Kinebuchi, M.; Miyakoshi,N.; Kitagaki, S.; Mukai
    • Organizer
      22ndInternational Congress on Heterocyclic Chemistry
    • Place of Presentation
      Delta hotel, St.John's, Newfounland and Labrador(Canada)
    • Year and Date
      2009-08-06
    • Related Report
      2010 Final Research Report
  • [Presentation] Synthetic studies on (+)-nakadomarin A2009

    • Author(s)
      Inagaki, F
    • Organizer
      22^<nd> International Congress on Heterocyclic Chemistry
    • Place of Presentation
      Delta Hotel St. John's (Canada)
    • Year and Date
      2009-08-06
    • Related Report
      2009 Annual Research Report

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

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