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Transition Metals-Mediated Efficient Synthesis of Biologically Active Natural Products.

Research Project

Project/Area Number 09672164
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionTokyo University of Pharmacy and Life Science

Principal Investigator

OHTA Akihiro  Tokyo University of Pharmacy and Life Science, School of Pharmacy, Professor, 薬学部, 教授 (90057307)

Co-Investigator(Kenkyū-buntansha) INABA Haruko  Tokyo University of Pharmacy and Life Science, School of Pharmacy, Research Fell, 薬学部, 助手 (40277257)
UCHIYAMA Masahiko  Tokyo University of Pharmacy and Life Science, School of Pharmacy, Research Fell, 薬学部, 助手 (40277265)
Project Period (FY) 1997 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1998: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1997: ¥1,600,000 (Direct Cost: ¥1,600,000)
KeywordsPalladium Catalyst / Pyrrole / Indole / beta-Hydroxy-enamine / Garner Aldehyde / (2R,3S)-2-Hydroxymethyl-3-hydroxypyrrolidine / (+)-Bulgecine / βーヒドロキシエナミン / Garner アルデヒド / (2R,3S)-2-hydroxymethyl-3-methylpyrrolidine / 合成 / L-セリン / バルジシニン / ピロリジン / 不斉オキシセレン化反応 / furo[2,3-b]furan誘導体 / Olean
Research Abstract

1. Palladium-Catalyzed Efficient Synthesis of Pyrroles and Indoles
Palladium-catalyzed oxidation of beta-hydroxy-enamine, which was easily prepared from amino alcohols and beta-keroesters, and subsequent cyclization gave the corresponding polysubstituted pyrroles in good yields. On the other hand, treatment of 2'-hydroxyethylaniline derivatives with palladium catalyst and mesityl bromide gave the corresponding 2-and 3-substituted indoles. 4-Oxo-5,6,7,8-tetrahydroindoles, which might be starting materials of ergot alkaloids, were also prepared under the same reaction conditions. The procedure developed in this project have several merits as shown below ; 1) catalytic amount of palladium salts is necessary, 2) catalysts could be recycled, 3) good yields, 4) starting materials are prepared easily or purchased, and 5) basic or almost neutral medium.
2. Chromium Chloride-Mediated Asymmetric Carbon-Carbon Bond Formation Reaction and its Synthetic Application to Biologically Active Natural Products
The Chromium(II) chloride-mediated coupling reactions of Garner aldehydes with allyl bromides gave the corresponding homoallyl alcohols in good yields with moderate to good stereoselectivity. Thus obtained homoallyl alcohols were converted to several biologically active natural products such as (2R,3S)-2-hydroxymethyl-3-hydroxypyrrolidine, (2R, 3R, 4R)-3-hydroxy-4-methylproline, and (+)-bulgecinine in short steps. We are also examining to synthesize sulfobacin now.

Report

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

    (7 results)

All Other

All Publications (7 results)

  • [Publications] Yutaka Aoyagi, Haruko Inaba, Akihiro Ohta: "Chromium (II) Chloride Mediated Coupling Reactions of Garner Aldehyde with Allyl Bromides : Facile Asymmetric Synthesis of (2R, 3S)-3-Hydroxy-2-hydroxymethylpyrrolidine" JOURNAL OF THE CHEMICAL SOCIETY PERKIN TRANSACTIONS 1. 23. 3975-3978 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yutaka Aoyagi, Toshihiko Mizusaki, Akihiro Ohta: "Facile and Efficient Synthesis of Pyrroles and Indolos via Palladium-Catalyzed Oxidation of Hydroxy-Enamines and -Amines" Tetraredron Letters. 37・51. 9203-9206 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yutaka Aoyagi, Haruko Inaba, Yukiko Hiraiwa, Akihiro Ohta: "Chromium (II) Chloride-Mediated Coupling Reactions of Garner Aldehyde with Allyl bromides : Facile Asymmetric Synthesis of (2R,3S)-3-Hydroxy-2-hydroxymethylpyrrolidine." J.Chem.Soc., Perkin Trans.1. 3975-3978 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yutaka Aoyagi, Toshihiko Mizusaki, Akihiro Ohta: "Facile and Efficient Synthesis of Pyrroles and Indoles via Palladium-Catalyzed oxidation of Hydroxy-Enamines and-Amines." Tetrahedron Lett.37. 9203-9206 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yutaka Aoyagi, Haruko Inaba, Akihiro Ohta: "Chromium(II)Chloride-Mediated Coupling Reactions of Garner Aldehyde with Allyl Bromides-Facile Asymmetric Synthesis of (2R,3S)-3-Hydroxy-2-hydroxymethylpyrrolidine" JOURNAL OF THE CHEMICAL SOCIETY PERKIN TRANSACTIONS 1. 23. 3975-3978 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Yutaka Aoyagi, Toshihiko Mizusaki, Akihiro Ohta: "Facile and Efficient Synthesis of Pgrroles and Indoles uia Palladium-Catalyzed Oxidation of Hydroxy-Enamines and-Amines" Tetrahedron Letters. 37・51. 9203-9206 (1996)

    • Related Report
      1998 Annual Research Report
  • [Publications] Yutaka Aoyagi, Tomomitsu Abe, Akihiro Ohta: "Facile and Efficient Deoxygenation of Aromatic N-Oxides with Zinc and Aqueous Ammonium Chloride" SYNTHESIS. 8. 891-894 (1997)

    • Related Report
      1997 Annual Research Report

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

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