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2006 Fiscal Year Final Research Report Summary

Synthesis of Biologically Active Alkaloids and Lead Compounds for Drug Development

Research Project

Project/Area Number 16390003
Research Category

Grant-in-Aid for Scientific Research (B)

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

Principal Investigator

NISHIDA Atsushi  Chiba University, Graduate School of Pharmaceutical Sciences, Professor, 大学院・薬学研究院, 教授 (80130029)

Project Period (FY) 2004 – 2006
Keywordslapidilectam / alkaloid / isomerization / cycloisomerization / indoline / ruthenium complex / fistulosin / manzamine A
Research Abstract

1.A new isomerization and cycloisomerization catalyst was developed by the reaction of Grubbs ruthenium carbine catalyst and trimethylsilyloxyvinylether. Using the catalyst, we developed a new method for the synthesis of indoles and 3-methyleneindolines. As an application of this reaction, we have succeeded in the synthesis of the putative structure of fistulosin which was isolated from the root or the Welsh onion and reported to have antifungal activity. Starting from 2-aminostylene, we have prepared the compounds and characterized by spectral means. However, the spectral data was not agree with those reported for fistulosin.
2.We have studied a total synthesis of Kopsia alkaloid lapidilectam and lundrine B. Although the biological activity of lapidilectam has not been reported, lundrine B has strong activity of anti-cancer activity. Based on the strategy developed by our group, central core was synthesized using Heck type cyclization with isomerization of olefin. Further study will be continued for the total synthesis.
3.Furan-iminium cation cyclization was developed. An application of this reaction has already been reported in the first total synthesis of nakadomarin A, a marine alkaloid isolated from sponge collected at Okinawa. Further study has been continued to clarify the scope and limitation of this reaction and we found that the reaction could be applied for other substrate. A new synthetic method for ircinal A, a biogenetical and synthetic intermediate for manzamine A, has been developed.

  • Research Products

    (14 results)

All 2006 2005

All Journal Article (13 results) Book (1 results)

  • [Journal Article] Synthesis of the Putative Structure of Fistulosin Using the Ruthenium-Catalyzed Cycloisomerization of Diene2006

    • Author(s)
      Yukiyoshi Terada, Mitsuhiro Arisawa, Atsushi Nishida
    • Journal Title

      Journal of Organic Chemistry 71・3

      Pages: 1269-1272

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Catalytic Asymmetric Michael Reaction under Phase-Transfer Catalysis; Construction of Chiral Tetrasubstituted Carbon and its Application to the Synthesis of a Chiral Pyrrolidone2006

    • Author(s)
      Shigeru Arai, Fumie Takahashi, Riichiro Tsuji, Atsushi Nishida
    • Journal Title

      Heterocycles 67

      Pages: 495-501

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Development of Novel Isomerization and Cycloisomerization using a Ruthenium Hydride with N-heterocyclic Carbene and Its Application to the Synthesis of Heterocycles2006

    • Author(s)
      Mitsuhiro Arisawa, Yukiyoshi Terada, Kazuyuki Takahashi, Atsushi Nishida
    • Journal Title

      J. Org. Chem. 71・11

      Pages: 4255-4261

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Catalytic Asymmetric Michael Reaction under Phase-Transfer Catalysis ; Construction of Chiral Tetrasubstituted Carbon and its Application to the Synthesis of a Chiral Pyrrolidone2006

    • Author(s)
      Shigeru Arai, Fumie Takahashi, Riichiro Tsuji, Atsushi Nishida
    • Journal Title

      Heterocycles 67-

      Pages: 495-501

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Synthesis of the Putative Structure of Fistulosin Using the Ruthenium-Catalyzed Cycloisomerization of Diene2006

    • Author(s)
      Yukiyoshi Terada, Mitsuhiro Arisawa, Atsushi Nishida
    • Journal Title

      Journal of Organic Chemistry 71-3

      Pages: 1269-1272

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Development of Novel Isomerization and Cycloisomerization using a Ruthenium Hydride with N-heterocyclic Carbene and Its Application to the Synthesis of Heterocycles2006

    • Author(s)
      Mitsuhiro Arisawa, Yukiyoshi Terada, Kazuyuki Takahashi, Atsushi Nishida
    • Journal Title

      Journal of Organic Chemistry 71-11

      Pages: 4255-4261

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Marine Natural Products2006

    • Author(s)
      Atsushi Nishida, Toshiaki Nagata, Masako Nakagawa
    • Journal Title

      Topics in Heterocyclic Chemistry 5

      Pages: 255-280

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Diastereoselective Fischer-Type Pyrroloindole Synthesis and Its Application to the Synthesis of Chiral Pyrroloindole Alkaloids2005

    • Author(s)
      Atsushi Nishida, Satoru Ushigome, Ayako Sugimoto, Shigeru Arai
    • Journal Title

      Heterocycles 66

      Pages: 181-185

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Preparation of N-Sulfonyl-2-quinolinone using Ring-Closing Metathesis (RCM)2005

    • Author(s)
      Mitsuhiro Arisawa, Chumpol Theeraladanon, Atsushi Nishida
    • Journal Title

      Heterocycles 66

      Pages: 683-668

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] A Facile Synthesis of Vicinal Diamines Promoted by Low-valent Niobium : Preparation of Chiral Octahydrobisisoquinolines and Their Application to Catalytic Asymmetric Synthesis2005

    • Author(s)
      Shigeru Arai, Satoshi Takita, Atsushi Nishida
    • Journal Title

      Euro. J. Org. Chem.

      Pages: 5262-5267

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Diastereoselective Fischer-Type Pyrroloindole Synthesis and Its Application to the Synthesis of Chiral Pyrroloindole Alkaloids2005

    • Author(s)
      Atsushi Nishida, Satoru Ushigome, Ayako Sugimoto, Shigeru Arai
    • Journal Title

      Heterocycles 66-

      Pages: 181-185

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Preparation of N-Sulfony1-2-quinolinone using Ring-Closing Metathesis (RCM)2005

    • Author(s)
      Mitsuhiro Arisawa, Chumpol Theeraladanon, Atsushi Nishida
    • Journal Title

      Heterocycles 66-

      Pages: 663-688

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] A Facile Synthesis of Vicinal Diamines Promoted by Low-valent Niobium : Preparation of Chiral Octahydrobisisoquinolines and Their Application to Catalytic Asymmetric Synthesis2005

    • Author(s)
      Shigeru Arai, Satoshi Takita, Atsushi Nishida
    • Journal Title

      Euro.Journal of Organic Chemistry

      Pages: 5262-5267

    • Description
      「研究成果報告書概要(欧文)」より
  • [Book] Marine Natural Products, Topics in Heterocyclic Chemistry2006

    • Author(s)
      Atsushi Nishida, Toshiaki Nagata, Masako Nakagawa
    • Total Pages
      255-280
    • Publisher
      Springer
    • Description
      「研究成果報告書概要(和文)」より

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Published: 2008-05-27  

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