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New Development of Photoelectron Transfer Reaction and its Application to Natural Product Synthesis

Research Project

Project/Area Number 61570987
Research Category

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

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

Principal Investigator

HAMADA Tatsuo  Faculty of Pharmaceutical Sciences, Hokkaido University, 薬学部, 助教授 (40001979)

Project Period (FY) 1986 – 1988
Project Status Completed (Fiscal Year 1988)
Budget Amount *help
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1988: ¥200,000 (Direct Cost: ¥200,000)
Fiscal Year 1987: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1986: ¥1,200,000 (Direct Cost: ¥1,200,000)
KeywordsPhotoelecron Transfer Reaction / Amino Protecting Group / Alcohol Protecting Group / アルコール保護基 / 天然物合成 / 光化学 / カンナビサチビン / トシル酸エステル
Research Abstract

Sinnce the concept of electron transfer was introduced into organic photochemistry a number of new reactions have been reported mainly from the mechanistic point of view. However, a few reactions involving the electron transfer in excited donor-acceptor pairs are generally useful in synthetic organic chemistry. Our research was conducted to develop new photelectron reaction to be useful in synthetic organic chemistry.
1e New Amino Protecting Group
The new anino protecting group like 1__- which have electron donor and acceptor was synthesized and was proved to be useful protecting group.
2) New Alcohol Protecting Group
Benzyltype protecting group like 2__- was examined and shown to be cleaved in high yield by irradiation with accepto (tetracyanoethylene et ct.) and separator of ion pair like magnesium perchloride.
3e Application to Natural Synthesis
Totalsynthesis of Palustrine 3__- and Cnnabisativine 4__- was tried and the synthesis of the inportant synthetic intermediate, 5__- and 6__- was completed and these will be converted to 3__- and 4__- respectively in several steps.
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Report

(4 results)
  • 1988 Annual Research Report   Final Research Report Summary
  • 1987 Annual Research Report
  • 1986 Annual Research Report
  • Research Products

    (22 results)

All Other

All Publications (22 results)

  • [Publications] T.Hamada,A.Nishida.;O.Yonemitsu.: Journal of American Chemical Society. 108. 140-145 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] T.Hamada.;O.Yonemitsu.: Synthesis. 852-854 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] N.Nakajima,;T.Hamada,;T.Tamaka.;Y.Oikawa.;O Yonemitsu.: Journal of American Chemical Society. 108. 4645-4647 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] T.Hamada,;A.Nishida.;O.Yonemitsu.: Tetrahedron Letters.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] A.Nishida,;T.Hamada.;O.Yonemitsu.: Journal of Organic Chemistry. 53. 3386-3387 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] T.Hamada; A.Nishida; O Yonemitsu: "Selective Removal of Electron-Accepting p-Toluene- and Naphthalenesulfonyl Protecting Groups for Amino Function via Photoinduced Donor-Acceptor Ion Pairs with Electron- Donating Aromatics" Journal of American Chemical Society. 108. 140-145 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] T.Hamada; O.Yonemitsu: "An Improved Synthesis of Arylsulfonyl Chrolides from ArylHalides" Synthesis. 852-854 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] N.Nakajima; T.Hamada; T.Tanaka; Y.Oikawa; O.Yonemitsu: "Stereoselective Synthesis of Picronolide, the Aglycon of the 14-Membered Ring Macrolide Picromycin, from D-Glucose. Role of MPM and DMPM Protection" Journal of American Chemical Society. 108. 4645-4647 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] T.Hamada; A.Nishida; O.Yonemitsu: "A New Amino Protecting Group Readily Removable with Near Ultraviolet Light as Application of Electron-Transfer Photochemistry" Tetrahedron Letters.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] A.Nishida; T.Hamada; O.Yonemitsu: "Hydrolysis of Tosyl Esters Initiated by an Elecron Transfer Photoexcited Electon-Rich Aromatic Compounds" Journal of Organic Chemistry. 53. 3386-3387 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] A.Nishida;T.Hamada;O.Yonemitsu: Journal of Origanic Chemistry. 53. 3386-3387 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] T.Hamada;A.Nishida;O.Yonemitsu: Tetrahedron letters. (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] T.Hamada;H.Sato;M.Hikota;O.Yonemitsu: Tetrahedron letters. (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] Tatsuo Hamada: Jounal of American Chemical Society.108. 140-145 (1986)

    • Related Report
      1987 Annual Research Report
  • [Publications] Noriyuki Nakajima: Journal of American Chemical Society. 108. 4645-4647 (1986)

    • Related Report
      1987 Annual Research Report
  • [Publications] Tatsuo Hamada: Synthesis. 852-854 (1986)

    • Related Report
      1987 Annual Research Report
  • [Publications] Atsushi Nishida: Submitted for publication Journal of Organic Chemistry.

    • Related Report
      1987 Annual Research Report
  • [Publications] Tatsuo Hamada: Submitted for publication Journal of xerican Chemical Society.

    • Related Report
      1987 Annual Research Report
  • [Publications] T.Hamada;A.Nishida;O.Yonemitsu.: The Journal of American Chemical Society. 108. 140-145 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] N.Nakajima;T.Hamada;T.Tanaka;Y.Oikawa;O.Yonemitsu: The Journal of American Chemical Society. 108. 4645-4647 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] T.Tanaka;Y.Oikawa;T.Hamada;O.Yonemitsu: Tetrahedron Letters. 27. 3651-3654 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] T.Hamada;O.Yonemitsu: Synthesis. 852-854 (1986)

    • Related Report
      1986 Annual Research Report

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Published: 1987-03-31   Modified: 2016-04-21  

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