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Development of Carbon-Carbon Bond Forming Reaction Utilizing New Mitsunobu Reagents

Research Project

Project/Area Number 13672244
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

TSUNODA Tetsuto  Tokushima Bunri University, Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (00172049)

Project Period (FY) 2001 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥3,100,000 (Direct Cost: ¥3,100,000)
Fiscal Year 2002: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2001: ¥2,200,000 (Direct Cost: ¥2,200,000)
KeywordsMitsunobu reaction / Cyanomethylenetrimethylphosphorane (CMMP) / Phosuphoranes / carbon-carbon bond formation / active methylene / 炭素-炭素結合合成
Research Abstract

The Mitsunobu reaction, a popular alkylation reaction utilizing the redox system between diethylazodicarboxylate and triphenylphosphine, has a shortcoming that it can only be applied satisfactorily to nucleophile (HA) of pK_u less than 11. In order to overcome the limitation, we introduced several combinations of azodicarboxamides (TIPA, ADDP, TMAD, and DHTD) and tributylphosphine. In our continual search for new versatile reagents, we found cyanomethylenetrialkylphosphorane (CMBP, CMMP) was capable of mediating the alkylation of various HA of larger pK_u than 11.
In our investigation, CMMP was found to be much more versatile in C-alkylation : it mediated the reaction of acids of pK_u【approximately equal】 23 (MT sulfone, benzyl phenyl sulfone, geranyl phenyl sulfone, etc.). Utilizing the C-alkylation reaction with these new reagents, we developed an efficient methodology for the synthesis of some biologically active compounds or their analogs, including pheromones, squalene synthetase inhibitors, and pyridine alkaloids.

Report

(3 results)
  • 2002 Annual Research Report   Final Research Report Summary
  • 2001 Annual Research Report
  • Research Products

    (12 results)

All Other

All Publications (12 results)

  • [Publications] Sho Ito: "New Mitsunobu Reagents in C-C Bond Formation. Application to Natural Product Synthesis"Pure & Appl.Chem.. 71・6. 1053-1057 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Kaori Uemoto: "Prenyl and geranyl phenyl sulfone, A new carbon nucleophile for Mitsunobu-type alkylation"Tetrahedron Lett.. 42・5. 905-907 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Izumi Sakamoto: "Preparation of (Cyanomethylene) trimethylphosphorane as a New Mitsunobu-Type Reagent"Chemical & Pharmaceutical Bulletin. 51・4(In press). (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Tetsuto Tsunoda: "My Favorite Organic Synthesis"The Society of Synthetic Organic Chemistry, Japan Kagaku-Dojin Publishing Co., Inc. Tokyo. 232-233 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] S. Ito and T. Tsunoda: "New Mitsunobu Reagents in C-C Bond Formation Application to Natural Product Synthesis"Pure & Appl. Chem.. 71(6). 1053-1057 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] K. Uemoto, A. Kawahito, N. Matsushita, I. Sakamoto, H.Kaku, and T. Tsunoda: "Prenyl and geranyl phenyl sulfone, A new carbon nucleophile for Mitsunobu-type alkylation"Tetrahedron Lett.. 42(5). 905-907 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] I. Sakamoto, H. Kaku, and T. Tsunoda: "Preparation of (Cyanomethylene)trimethylphosphorane as a New Mitsunobu-Type Reagent"Chem. Pharm. Bull.. 51(4), in press. (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] T. Tsunoda, Eds. By The Society of Synthetic Organic Chemistry: "New Redox System for the Mitsunobu Reaction, My Favorite Organic Synthesis"Japan, Kagaku-Dojin Publishing Co., Inc. Tokyo. 232--233 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Izumi Sakamoto: "Preparation of (Cyanomethylene)trimerhylphosphorane as a New Mitsunobu-Type Reagent"Chemical & Pharmaceutical Bulletin. 51・4. (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] Tetsuto Tsunoda: "My Favorite Organic Synthesis"The Society of Synthetic Organic Chemistry, Japan Kagaku-Dojin Publishing Co., Inc. Tokyo. 232-233 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Sho Ito: "New Mitsunobu Reagents in C-C Bond Formation. Application to Natural Product Synthesis"Pure & Appl.Chem.. 71.6. 1053-1057 (1999)

    • Related Report
      2001 Annual Research Report
  • [Publications] Kaori Uemoto: "Prenyl and geranyl phenyl sulfone, A new carbon nucleophile for Mitsunobu-type alkylation"Tetrahedron Lett.. 42.5. 905-907 (2001)

    • Related Report
      2001 Annual Research Report

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Published: 2001-04-01   Modified: 2016-04-21  

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