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Studies on benzo [c] phenanthridine alkaloid using novel palladium reagents

Research Project

Project/Area Number 09672144
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

HARAYAMA Takashi  Faculty of Pharmaceutical Sciences, Okayama University Profesor, 薬学部, 教授 (30025712)

Project Period (FY) 1997 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥2,900,000 (Direct Cost: ¥2,900,000)
Fiscal Year 1998: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 1997: ¥1,800,000 (Direct Cost: ¥1,800,000)
Keywordspalladium reagent / chelerythrine / nitidine / benzo [c] phenanthridine / benzo [d] naphthopyranone / biaryl coupling reaction / ベンゾ[C]フェナンスリジン
Research Abstract

1) Development of general synthetic method for benzo[c]phenanthridine alkaloid using novel palladium reagents
A novel palladium reagent prepared from equimolar Pd(OAc)_2, DPPP, and Bu3P was useful for the internal biaryl coupling reaction of not only triflate-amide but also halo-amide as leaving group. By using this novel Pd reagent, benzo[c]phenanthridine alkaloids, chelerythrine and nitidine were synthesized in good yields.
2) Synthetic studies on benzo[d]naphthopyranones
Benzo[d]naphthopyranones, arnottin I, was synthesized by using typical Heck* s reaction conditions.
3) Synthetic studies on phenanthridine alkaloids
Phenanthridine alkaloid, trisphaeridine, was synthesized via biaryl coupling reaction using palladium reagent.
4) Mechanistic aspect of novel Palladium reagent [Pd(OAc)_2-PPP-Bu_3P]
It was found out that molar ratio of Pd phosphine = 1 : 3 is essentially necessary for biaryl coupling reaction

Report

(3 results)
  • 1998 Annual Research Report   Final Research Report Summary
  • 1997 Annual Research Report
  • Research Products

    (12 results)

All Other

All Publications (12 results)

  • [Publications] Takashi Harayama: "Internal Aryl-aryl Coupling Reaction Using a Novel and Highly Active Palladium Reagent Prepared from Pd(OAc)_2, DPPP, and Bu_3P" Chemical & Pharmaceutical Bulletin. 45・10. 1723-1725 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Takashi Harayama: "A Concise Synthesis of Arnottin I via Internal Biaryl Coupling Reaction Using Palladium Reagent" Heterocycles. 46. 61-64 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Takashi Harayama: "Synthesis of Benzo[c]phenanthridine Alkaloids, Chelerythrine and Nitidine Using a Novel Palladium-Phosphine Combination System-Pd(OAc)_2, DPPP, and Bu_3P" Heterocycles. 48・10. 1989-1993 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Takashi Harayama: "Concise Synthesis of Nitidine by Palladium-assisted Biaryl Coupling Reaction" Heterocycles. 49. 191-195 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Takashi Harayama: "Internal Aryl-aryl Coupling Reaction Using a Novel and Highly Active Palladium Reagent Prepared from Pd (OAc) _2, DPPP,and Bu_3P" Chemical & Pharmaceutical Bulletin. 45 (10). 1723-1725 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Takashi Harayama: "A Concise Synthesis of Arnottin I via Internal Biaryl Coupling Reaction Using Palladium Reagent" Heterocycles. 46. 61-64 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Takashi Harayama: "Synthesis of Benzo [c] phenanthridine Alkaloids, Chelerythrine and Nitidine Using a Novel Palladium-Phosphine Combination System-Pd (OAc) _2, DPPP,and Bu_3P" Heterocycles. 48 (10). 1989-1993 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Takashi Harayama: "Concise Synthesis of Nitidine by Palladium-assisted Biaryl Coupling Reaction" Heterocycles. 49. 191-195 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Takashi Harayama: "Synthesis of Benzo [C] phenanthridine Alkaloids, Chelerythrine and Nitidine Using a Novel palladium-Phosphine Combination System-Pd (OAc)_2, DPPP, and Bu_3P" Heterocycles. 48・10. 1989-1993 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Takashi Harayama: "Concise Synthesis of Nitidine by Palladium-assisted Biaryl Coupling Reaction" Heterocycles. 49. 191-195 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Takashi Harayama: "Internal Aryl-aryl Coupling Reaction Using a Novel and Highly Active Palladium Reagent Prepared from Pd(OAc)_2,DPPP,and Bu_3P" Chemical & Pharmceutical Bulletin. 45・10. 1723-1725 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Takashi Harayama: "A Concise Synthesis of Arnottin I via Internal Biaryl Coupling Reaction Using Palladium Reagent" Heterocycles. 46. 61-64 (1997)

    • Related Report
      1997 Annual Research Report

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Published: 1997-04-01   Modified: 2016-04-21  

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