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2010 Fiscal Year Final Research Report

Synthetic Studies toward Kinamycin-Jadomycin Antibiotics

Research Project

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Project/Area Number 20590002
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

KUMAMOTO Takuya  Musashino University, 薬学研究所, 教授 (50292678)

Project Period (FY) 2008 – 2010
Keywordsキナマイシン / ロマイビチシン / ジャドマイシン / グアニジン / 二量化反応
Research Abstract

Total syntheses of prekinamycin and jadomycin A were achieved via "naphthalene route", Suzuki-Miyaura coupling of bromonaphthalene unit as AB ring and phenylboronic acid as D ring part. C ring formation of AB-D ring unit followed by diazotization lead to the synthesis of the former compound. The latter was synthesized by introduction of isoleucine and deprotection. The basic carbon skeleton of kinamycins was also achieved by introduction of oxygen functionality on D ring of same synthetic intermediate of prekinamycin.

  • Research Products

    (14 results)

All 2011 2010 2009 2008

All Journal Article (4 results) (of which Peer Reviewed: 4 results) Presentation (8 results) Book (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] (Syntheses of prekinamycin and tetracyclic quinone from common synthetic intermediates.2011

    • Author(s)
      Kimura S.; Kobayashi S.; Kumamoto T.
    • Journal Title

      Helv.Chim.Acta 94巻

      Pages: 578-591

    • Peer Reviewed
  • [Journal Article] キナマイシン系抗生物質の全合成研究2011

    • Author(s)
      熊本卓哉
    • Journal Title

      薬学雑誌 130巻

      Pages: 1535-1541

    • Peer Reviewed
  • [Journal Article] Synthetic studies on jadomycins : synthesis of dimethyljadomycin A2010

    • Author(s)
      Akagi Y.
    • Journal Title

      Tetrahedron Lett. 51巻

      Pages: 1338-1341

    • Peer Reviewed
  • [Journal Article] Diels-Alder reactions using 4,7-dioxygenated indanones as dienophiles for regioselective construction of oxygenated 2,3-dihydrobenz[f]indenone skeleton.2008

    • Author(s)
      Etomi N,; Kumamoto T.; Nakanishi W.; Ishikawa T.
    • Journal Title

      Beilstein J.Org.Chem. 4巻

      Pages: No.15

    • Peer Reviewed
  • [Presentation] ジャドマイシン系抗生物質の合成研究:ジャドマイシンAの全合成2011

    • Author(s)
      田島孝祐,赤木祐介,山田紳一郎,江富なつの,熊本卓哉,石川勉
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Year and Date
      2011-03-31
  • [Presentation] ジャドマイシン類の合成研究2010

    • Author(s)
      田島孝祐,赤木祐介,山田紳一郎,江富なつの,熊本卓哉,石川勉
    • Organizer
      第52回天然有機化合物討論会
    • Place of Presentation
      静岡
    • Year and Date
      2010-09-30
  • [Presentation] キナマイシン類の網羅的全合成に向けたプレキナマイシンの合成研究(2)2010

    • Author(s)
      木村槙吾,熊本卓哉,石川勉
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山大学
    • Year and Date
      2010-03-29
  • [Presentation] ジャドマイシン系抗生物質の合成研究2010

    • Author(s)
      赤木祐介,熊本卓哉,石川勉
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山大学
    • Year and Date
      2010-03-28
  • [Presentation] Kinamycin系抗生物質の合成研究2009

    • Author(s)
      熊本卓哉
    • Organizer
      第53回日本薬学会関東支部会
    • Place of Presentation
      城西大学(奨励賞受賞講演)
    • Year and Date
      2009-10-03
  • [Presentation] 抗菌・抗腫瘍活性キナマイシン類の網羅的全合成研究2009

    • Author(s)
      木村槙吾,熊本卓哉,石川勉
    • Organizer
      第57回有機合成化学協会関東支部シンポシウム
    • Place of Presentation
      早稲田大学
    • Year and Date
      2009-05-09
  • [Presentation] キナマイシン類の網羅的全合に向けたプレキナマイシンの合成研究2009

    • Author(s)
      木村槙吾,熊本卓哉,石川勉
    • Organizer
      第129日本薬学会年会
    • Place of Presentation
      京都
    • Year and Date
      2009-03-27
  • [Presentation] 抗菌活性Kinamycin類の合成研究,(±)-Methyl-kinamycin Cの全合成2008

    • Author(s)
      熊本卓哉
    • Organizer
      第12回がん分子標的治療研究会総会
    • Place of Presentation
      東京
    • Year and Date
      2008-06-26
  • [Book] Superbases for Organic Synthesis, Guanidines, Amidines, Phosphazenes and Related Organocatalysts2009

    • Author(s)
      石川勉(編),熊本卓哉(共著)
    • Total Pages
      41-91, 295-313
    • Publisher
      John Wiley & Sons
  • [Patent(Industrial Property Rights)] グアニジン化合物及びグアニジン化合物のポリマー固定化複合体2010

    • Inventor(s)
      石川勉,平馬崇,熊本卓也(卓哉)
    • Industrial Property Rights Holder
      千葉大学
    • Industrial Property Number
      公開特許公報(A),特許公開2010-111633
    • Acquisition Date
      2010-05-20

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Published: 2012-01-26   Modified: 2021-09-16  

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