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Biologically Active Substances by Use of Electrochemical Oxidation Associate Professor

Research Project

Project/Area Number 01571133
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionHokkaido University

Principal Investigator

MORI Miwako  Faculty of Pharmaceutical Sciences, Hokkaido University, 薬学部 助教授 (80001981)

Project Period (FY) 1989 – 1990
Project Status Completed (Fiscal Year 1990)
Budget Amount *help
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1990: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 1989: ¥1,200,000 (Direct Cost: ¥1,200,000)
KeywordsElectrochemical Reaction / Anodic Oxidation / gamma-Lactam / alpha-Acetoxy-gamma-lactam / γーラクタム / αーアセトキシーγーラクタム / γ-ラクタム / α-アセトキシ-γ-ラクタム
Research Abstract

Anodic oxidation of lactoms was very useful for the synthetic organic chemistry. We have already reported the new synthetic method of 4-acetoxy-2-azatidinones from 4-carboxy-2-azetidinones by use of electrochemical oxidation. Namely, 4-carboxy-2-azatidinone was electrolyzed in an undivided cell using platinum plates as electrode in the presence of AcONa as electrolyte in AcOH-CH_3CN to give 4-acetoxy-2-azetidinone in high yield. Using this method, a new synthetic method of optically active 3-hydroxy-ethyl-4-acetoxy-2-azetidinone which was an intermediate for the synthesis of thienamycin and its analogues, was developed and a formal total synthesis of (+)-PS-5 was achieved. This method was applied for the synthesis of gamma-lactams. Pyroglutamic acid was electrolyzed to afford 2-acetoxy-pyrrolldone in good yield. In a similar manner, compounds2a and 2b were obtained from 1a and 1b. Subsequently, C-C bond formation at 2-position of pyrrolldone was tried. Compound 6__- which was obtained by electrolysis from compound 5__- was treated with TiCl_4 to provide indollzidine derivative in good yield. Thus, the new method for the synthesis of bicyclic lactams by electrolysis from lactams having carboxy group at alpha-position of nitrogen was developed.

Report

(3 results)
  • 1990 Annual Research Report   Final Research Report Summary
  • 1989 Annual Research Report
  • Research Products

    (7 results)

All Other

All Publications (7 results)

  • [Publications] Miwako Mori: "Ring Construction of Bicyclic bataーLactam by Use of Palladium Catalyzed Carbonylation" Heterocyles. 29. 853-856 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Miwako Mori: "Ring Constrction of alphaーLactam by Use of Electrochemical Oxidation" Heterocycles. 29. 2089-2092 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Miwako Mori: "New Systhesis of 4ーAcetoxyー2ーAzetidinones by Use of Electrochemical Oxidation" Tetrahedron. 47. 531-540 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] M. Mori: "Ring Construction of Bicyclic beta-lactams by Use of Palladium Catalyzed Carbonylation" Heterocycles. 29. 853 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] M. Mori: "Ring Construction off Bicyclic gamma-Lactams by Use of Electrochemical Oxidation" Heterocycles. 29. 2089 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] M. Mori: "New Synthesis of 4-Acetoxy-2-azetidinones by Use of Electrochemical Oxidation" Tetrahedron. 47. 531 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Miwako Mori: "Ring Construction of Bicyclic γ-Lactams by Use of Electrochemical Oxidation" Heterocycles. 29. 2089-2092 (1989)

    • Related Report
      1989 Annual Research Report

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Published: 1989-04-01   Modified: 2016-04-21  

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