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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
Project Status Completed (Fiscal Year 2006)
Budget Amount *help
¥13,000,000 (Direct Cost: ¥13,000,000)
Fiscal Year 2006: ¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2005: ¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2004: ¥5,800,000 (Direct Cost: ¥5,800,000)
Keywordslapidilectam / alkaloid / isomerization / cycloisomerization / indoline / ruthenium complex / fistulosin / manzamine A / 相関移動触媒 / ピロリドン / ジアゾエステル / 異性化反応 / 環化異性化反応 / Grubbs触媒 / インドール / ルテニウム錯体 / ナカドマリンA / 閉環メタセシス / Diels-Alder反応 / フラン / ルテニウム / カルベン錯体
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.

Report

(4 results)
  • 2006 Annual Research Report   Final Research Report Summary
  • 2005 Annual Research Report
  • 2004 Annual Research Report
  • Research Products

    (25 results)

All 2006 2005 2004

All Journal Article (24 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
    • Related Report
      2006 Final Research Report Summary 2005 Annual Research Report
  • [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
    • Related Report
      2006 Final Research Report Summary
  • [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
    • Related Report
      2006 Final Research Report Summary
  • [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
    • Related Report
      2006 Final Research Report Summary
  • [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
    • Related Report
      2006 Final Research Report Summary
  • [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
    • Related Report
      2006 Final Research Report Summary
  • [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
    • Related Report
      2006 Final Research Report Summary
  • [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巻

      Pages: 495-501

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Synthesis of α-Diazo-β-hydroxyesters through a One-Pot Protocol by Phase-Transfer Catalysis : Application to Enantioselective Aldol-Type Reaction and Deastereoselective Synthesis of α-Amino-β-hydroxyester Derivatives2006

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

      Tetrahedron 62巻

      Pages: 1390-1401

    • Related Report
      2006 Annual Research Report
  • [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巻

      Pages: 4255-4261

    • Related Report
      2006 Annual Research Report
  • [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

    • NAID

      40007080613

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary 2005 Annual Research Report
  • [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

    • NAID

      40007080663

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [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
    • Related Report
      2006 Final Research Report Summary
  • [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

    • NAID

      40007080613

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [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
    • Related Report
      2006 Final Research Report Summary
  • [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
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Preparation of N-Sulfonyl-2-quinolinone using Ring-Closing Metathesis (RCM)2005

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

      Heterocycles 66

      Pages: 683-668

    • NAID

      40007080663

    • Related Report
      2005 Annual Research Report
  • [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

    • Related Report
      2005 Annual Research Report
  • [Journal Article] A Novel Synthesis of Substituted Quinolines Using Ring-Closing Metathesis (RCM) : Its Application to the Synthesis of Key Intermediates for Anti-malarial Agents2004

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

      Tetrahedron Vol.68

      Pages: 3017-3035

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Asymmetric Total Synthesis of (-)-Nakadomarin A2004

    • Author(s)
      Koji Ono, Masako Nakagawa, Atsushi Nishida
    • Journal Title

      Angew.Chem.Int.Ed. Vol.43,No.15

      Pages: 2020-2023

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Cycloisomerization Promoted by the Combination of a Ruthenium Carbene Catalyst and Vinyloxytrimethylsilane, and its Application to the Synthesis of Heterocyclic Compounds ; 3-Methylene-2,3-dihydroindoles and 3-Methylene-2,3-dihydrobenzofurans2004

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

      Angew.Chem.Int.Ed. Vol.43,No.31

      Pages: 4063-4067

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Novel Synthesis of Fused Indoles by the Palladium-Catalyzed Cyclization of N-Cycloalkenyl-o-haloanilines2004

    • Author(s)
      Takeshi Watanabe, Shigeru Arai, Atsushi Nishida
    • Journal Title

      Synlett

      Pages: 907-909

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Effect of Synthetic Sphingosine-1-phoshate analogs on Arachidonic Acid Metabolism and Cell Death2004

    • Author(s)
      Hiroyuki Nakamura, Yuko Takashiro, Tetsuya Hirabayashi, Syunji Horie, Yuuki Koide, Atsushi Nishida, Toshihiko Murayama
    • Journal Title

      Biochemical Pharmacology Vol.68

      Pages: 2187-2196

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Total Synthesis of (+)-(S)-Angustureine and Determination of the Absolute configuration of the Natural Product Angustureine2004

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

      Tetrahedron Asymmetry Vol.16

      Pages: 827-831

    • Related Report
      2004 Annual Research Report
  • [Book] Marine Natural Products, Topics in Heterocyclic Chemistry2006

    • Author(s)
      Atsushi Nishida, Toshiaki Nagata, Masako Nakagawa
    • Publisher
      Springer
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary

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Published: 2004-04-01   Modified: 2016-04-21  

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