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Synthetic Studies on Biologically Active Poly-Functionalized Carbazoles

Research Project

Project/Area Number 07672303
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

HIBINO Satoshi  Fukuyama University Faculty of Pharmacy and Pharmaceutical Sciences Professor, 薬学部, 教授 (60112885)

Co-Investigator(Kenkyū-buntansha) SUGINO Eiichi  Fukuyama University Faculty of Pharmacy and Pharmaceutical Sciences Associate Pr (00179144)
CHOSHI Tominari  Fukuyama University Faculty of Pharmacy and Pharmaceutical Sciences Research Ass (10248297)
Project Period (FY) 1995 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 1996: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1995: ¥600,000 (Direct Cost: ¥600,000)
Keywordscarbazole alkaloid / carazostatin / hyellazole / carbazoquinocins B-F / synthesis / electrocyclic reaction / allene intermediate / oxazolocarbazole
Research Abstract

1. The free radical scavenger carazostatin and the marine alkaloid hyellazole have been synthesized by a new type of allene-mediated electrocyclic reaction involving the indole 2,3-bond as a key step.
2. New tetracyclic oxazolo [4,5-c] carbazole and oxazolo [5,4-c] carbazole ring systems as functionalized precursors to antioxidative antiostatins (A_<1-4> and B_<2-5>) and carbazoquinocins (A-F) were synthesized.
3. A new benzo-annelation method based on the allene-mediated electrocyclic reaction of 2,3-functionalized indoles provides an effective route to the highly-functionalized carbazole ring, and the total syntheses of carazostatin, hyellazole and carbazoquinocins B to F have been completed. Moreover, the first total syntheses of carbazoquinocins B,C,E and F were demonstrated.

Report

(3 results)
  • 1996 Annual Research Report   Final Research Report Summary
  • 1995 Annual Research Report
  • Research Products

    (10 results)

All Other

All Publications (10 results)

  • [Publications] 日比野俐: "Total Syntheses of Carazostatin and Hyellazole by Allene-Mediated Electrocyclic Reaction" Tetrahedron Letters. 37. 2593-2596 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 日比野俐: "Synthesis of New Tetracyclic Oxazolocarbazoles as Functionalized Precursors to Antioxidative Agents, Antiostatins" Heterocycles. 43. 1847-1854 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 日比野俐: "Total Syntheses of Carazostatin, Hyellazole and Carbazoquinocins B to F" The Journal of Organic Chemistry. 62(in press). (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Tominari Choshi, Takuya Sada, Hiroyuki Fujimoto, Chizu Nagayama, Eiichi Sugino, and Satoshi Hibino: "Total Syntheses of Carazostatin and Hyellazole by Allene-Mediated Electrocyclic Reaction" Tetrahedron Letters. Vol.37 No.15. 2593-2596 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Tominari Choshi, Hiroyuki Fujimoto, Eiichi Sugino, and Satoshi Hibino: "Synthesis of New Tetracyclic Oxazolocarbazoles as Functionalized Precursors to Antioxidative Agents, Antiostatins and Carbazoquinocins" Heterocycles. Vol.43 No.9. 1847-1854 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Tominari Choshi, Takuya Sada, Hiroyuki Fujimoto, Chizu Nagayama, Eiichi Sugino, and Satoshi Hibino: "Total Syntheses of Carazostatin, Hyellazole and Carbazoquinocins B to F" J.Org. Chem.Vol.62(in press). (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 日比野俐他: "Total Syntheses of Carazostatin and Hyellazole by Allene-Mediated Electrocyclic Reactions" Tetrahedron Letters. 37,15. 2593-2596 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] 日比野俐他: "Synthesis of New Tetracyclic Oxazolocarbazoles as Functionalized Precursors to Antioxidative Agents,Antiostatins and Carbazoquinocis" Heterocycles. 43,9. 1847-1854 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] 日比野俐他: "Total Syntheses of Carazostatin,Hyellazole and Carbazoquinocins B to F" J.Org.Chem.(in press). (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] 日比野 俐: "Total Syntheses of Carazostatin and Hyellazole by Allene-Mediated Electrocyclic Reaction" Tetrahedron Letters. 37(印刷中). (1996)

    • Related Report
      1995 Annual Research Report

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Published: 1995-04-01   Modified: 2016-04-21  

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