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Synthetic and bioorganic studies on Ciguatoxin and Tetrodotoxin acting to sodium channel protein

Research Project

Project/Area Number 14360063
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionNagoya University

Principal Investigator

ISOBE Minoru  Nagoya University, Graduate School of Bioagricultural Sciences, Professor, 大学院・生命農学研究科, 教授 (00023466)

Project Period (FY) 2002 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥14,800,000 (Direct Cost: ¥14,800,000)
Fiscal Year 2003: ¥6,300,000 (Direct Cost: ¥6,300,000)
Fiscal Year 2002: ¥8,500,000 (Direct Cost: ¥8,500,000)
Keywordsciguatoxin / acetylene / biscobalt-hexacarbonyl / tetrodotoxin / cyclization / regioselectivity / hydrosylilation / sodium channel
Research Abstract

This research includes two major natural products conducting the ion current in the sodium channel protein ; thus, ciguatoxin and tetrodotoxin. Total synthesis of the latter has been accomplished by 2 routes initiated by Claisen rearrangement or Diels-Alder cycloaddition from 2 different sugar derivatives, respectively. These routes are different with respect to the key reactions, and thus both of them are quite useful for the further bioorganic studies. On the other hand, the synthetic studies on ciguatoxin has been culminated to a point of synthesizing Left segment, Right segment and their model coupling reaction by means of acetylene biscobalt-hexacarbonyl chemistry. The crytical step is the formation of F and G rings after the coupling step. We have developed an important reaction for conversion of the cobalt complex into the requisited ketone with regioselectivity. We have also established the catalytic amount of cobalt reagent to achieve 4 steps in one pot ; thus, complexation, hydrosylilation, cyclization and decomplexation with stereochemical control.

Report

(3 results)
  • 2003 Annual Research Report   Final Research Report Summary
  • 2002 Annual Research Report
  • Research Products

    (27 results)

All Other

All Publications (27 results)

  • [Publications] M.Isobe et al.: "Synthesis of JKLM Ring Fragment of Ciguatoxin 1B via Acetylene-Cobalt Strategy."Synlett. 547-551 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Isobe et al.: "Convergent Synthesis of the E'FGH Ring Fragment of Ciguatoxin 1B via an Acetylene Cobalt Complex Strategy"J. Org. Chem.. 68. 3225-3231 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Isobe et al.: "The First Total Synthesis of (-)-Tetrodotoxin."J. Am. Chem. Soc.. 125. 8798-8805 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Isobe et al.: "Synthesis of the JKLM-ring fragment of ciguatoxin."Tetrahedron. 59. 6851-6872 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Isobe et al.: "Different C-Glycosidation products of glucal with alkynyl or propargyl silanes under acidic conditions."Org. Lett.. 5. 4883-4885 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Isobe et al.: "Stereoselective synthesis of the fully functionalized HIJ-ring framework of ciguatoxin"Synlett. 603-608 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] 金久保 暁, 久世 雅樹, 磯部 稔: "「化学と生物」連載講座「発光物質が語るバイオサイエンス」"社団法人 日本農芸化学会. 19 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Isobe et al.: "Synthesis of JKLM Ring Fragment of Ciguatoxin 1B via Acetylene-Cobalt Strategy."Synlett. 547-551 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Isobe et al.: "Convergent Synthesis of the E'FGH Ring Fragment of Ciguatoxin 1B via an Acetylene Cobalt Complex Strategy."J.Org.Chem.. 68. 3225-3231 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Isobe et al.: "The First Total Synthesis of (-)-Tetrodotoxin."J.Am.Chem.Soc.. 125. 8798-8805 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Isobe et al.: "Synthesis of the JKLM-ring fragment of Ciguatoxin."Tetrahedron. 59. 6851-6872 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Isobe et al.: "Different C-Glycosidation products of glucal with alkynyl or propargyl silanes under acidic conditions."Org.Lett.. 5. 4883-4885 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Isobe et al.: "Stereoselective synthesis of the fully functionalized HIJ-ring framework of ciguatoxin."Synlett. 603-608 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Isobe et al.: "Synthesis of JKLM Ring Fragment of Ciguatoxin 1B via Acetylene-Cobalt Strategy."Synlett. 547-551 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Isobe et al.: "Convergent Synthesis of the E'FGH Ring Fragment of Ciguatoxin 1B via an Acetylene Cobalt Complex Strategy"J.Org.Chem.. 68. 3225-3231 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Isobe et al.: "The First Total Synthesis of (-)-Tetrodotoxin."J.Am.Chem.Soc.. 125. 8798-8805 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Isobe et al.: "Synthesis of the JKLM-ring fragment of ciguatoxin."Tetrahedron. 59. 6851-8805 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Isobe et al.: "Different C-Glycosidation products of glucal with alkynyl or propargyl silanes under acidic conditions."Org.Lett.. 5. 4883-4885 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Isobe et al.: "Stereoselective synthesis of the fully functionalized HIJ-ring framework of ciguatoxin"Synlett. 603-608 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] 金久保 暁, 久世 雅樹, 磯部 稔: "「化学と生物」連載講座「発光物質が語るバイオサイエンス」"社団法人 日本農芸化学会. 19 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Isobe et al.: "Synthesis of the BCD-ring of Ciguatoxin 1B using an acetylene cobalt complex and vinylsilane strategy"Tetrahedron. 58. 1875-1888 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.Isobe et al.: "Sodium Hypophosphite Decompl exation of Acetylenebiscobal thexacarbonyls to cis-Olefins"Synlett. 588-592 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.Isobe et al.: "Convergent Synthesis of the E'FGH'ring fragment of ciguatoxin 1B via an acetylene cobalt complex strategy"Organic Letters. 4. 1183-1186 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.Isobe et al.: "Mechanistic Studies on the Hydrosilylation of an Acetylene cobalt and O-Silylation"Tetrahedron. 58. 6485-6492 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.Isobe et al.: "Asymmetric Total Synthesis of 11-Deoxytetrodotoxin, a Naturally Occurring Congener"J. Am. Chem. Soc. 124. 7847-7852 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.Isobe et al.: "Stereocontrolled Synthesis of 8, 11-Dideoxytetrodotoxin, Uunatural Analog of Puffer Fish Toxin"Organic Letters. 4(#16). 2679-2680 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Witczak, Z.J., Tatsuta, K.: "Carbohydrate Synthons in Natural Products Chemistry Synthesis, Functionalization, and Applications"American Chemical Society. Washington, DC. 841 (2003)

    • Related Report
      2002 Annual Research Report

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Published: 2002-04-01   Modified: 2016-04-21  

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