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Synthetic study toward lomaiviticin A with dimerization of the substrate with flexible structure

Research Project

Project/Area Number 23590018
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionMusashino University

Principal Investigator

KUMAMOTO Takuya  武蔵野大学, 薬学研究所, 教授 (50292678)

Project Period (FY) 2011-04-28 – 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 2013: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2012: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2011: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Keywordsロマイチビチン / 抗生物質 / 抗腫瘍活性 / Michael 反応 / Dieckmann 縮合 / 二量化反応 / 鈴木-宮浦カップリング / ロマイビチシン / 二量化 / Michael-Dieckman 連続反応 / Diels-Alder 反応 / 鈴木-宮浦カップリング / 2量化反応
Outline of Final Research Achievements

Toward synthetic study towards antitumor antibiotic lomaiviticin A with dimeric structure, the synthesis of the substrate for the dimerization was explored, which has a structurally flexible 2-aryl cyclohexane derivative before the construction of 5-membered B-ring with suitable solubility for dimerization condition. Substrate for the dimerization was obtained with Suzuki coupling of bromocyclohexenone and Nagata reagent but dimerization at a desired position was not observed. On the other hand, D ring construction from cinnamic acid ester and furanone was achieved by Michael-Dieckmann continuous reaction.

Report

(5 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • 2011 Research-status Report
  • Research Products

    (6 results)

All 2015 2014 2013 Other

All Presentation (5 results) (of which Invited: 2 results) Remarks (1 results)

  • [Presentation] 抗菌・抗腫瘍活性 Lomaiviticin A の合成研究 : 環化付加反応によるD環構築の試み2015

    • Author(s)
      小幡七瀬,片川和明,熊本卓哉
    • Organizer
      日本薬学会第135年会
    • Place of Presentation
      神戸学院大学
    • Year and Date
      2015-03-26 – 2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] 抗菌・抗腫瘍活性 Lomaiviticin A の合成研究 環化付加反応によるD環構築の試み2014

    • Author(s)
      小幡七瀬,片川和明,熊本卓哉
    • Organizer
      第58回日本薬学会関東支部大会
    • Place of Presentation
      昭和薬科大学
    • Year and Date
      2014-10-04
    • Related Report
      2014 Annual Research Report
  • [Presentation] Synthetic Studies toward Natural Products with Oligomeric Structure2013

    • Author(s)
      熊本卓哉
    • Organizer
      日本薬学会北陸支部特別講演会
    • Place of Presentation
      金沢大学(石川)
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] Synthetic Studies toward Natural Products with Oligomeric Structure2013

    • Author(s)
      熊本卓哉
    • Organizer
      Ruder Boskovic 研究所講演会
    • Place of Presentation
      Ruder Boskovic 研究所(クロアチア,ザグレブ)
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] Synthetic Studies of Kinamycin Antibiotics and Related Compounds

    • Author(s)
      Kumamoto, T.; Kitani, Y.; Tsuchiya, H.; Kimura, S.; Ishikawa, T.
    • Organizer
      AIMECS 11: The 8th AFMC International Medicinal Chemistry Symposium "Frontier of Medicinal Science"
    • Place of Presentation
      東京(京王プラザホテル)
    • Related Report
      2011 Research-status Report
  • [Remarks] 本研究の発端となったプレキナマイシン合成に関する論文が Helv. Chim. Acta 誌の the 10 most-frequently accessed articles となった.(平成24年5月時点)

    • URL

      http://onlinelibrary.wiley.com/journal/10.1002/%28ISSN%291522-2675/homepage/MostAccessed.html

    • Related Report
      2011 Research-status Report

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Published: 2011-08-05   Modified: 2019-07-29  

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