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Total Synthesis of Ciguatoxins and Studies on The Antibodies and The Mechanism of Action

Research Project

Project/Area Number 14103019
Research Category

Grant-in-Aid for Scientific Research (S)

Allocation TypeSingle-year Grants
Research Field Bioorganic chemistry
Research InstitutionTohoku University

Principal Investigator

HIRAMA Masahiro  Tohoku University, Graduate School of Science, Professor, 大学院理学研究科, 教授 (30165203)

Co-Investigator(Kenkyū-buntansha) INOUE Masayuki  Tohoku University, Graduate School of Science, Associate Professor, 大学院理学研究科, 助教授 (70322998)
大栗 博毅  東北大学, 大学院・理学研究科, 助手 (80311546)
Project Period (FY) 2002 – 2006
Project Status Completed (Fiscal Year 2006)
Budget Amount *help
¥111,800,000 (Direct Cost: ¥86,000,000、Indirect Cost: ¥25,800,000)
Fiscal Year 2006: ¥22,100,000 (Direct Cost: ¥17,000,000、Indirect Cost: ¥5,100,000)
Fiscal Year 2005: ¥22,100,000 (Direct Cost: ¥17,000,000、Indirect Cost: ¥5,100,000)
Fiscal Year 2004: ¥22,100,000 (Direct Cost: ¥17,000,000、Indirect Cost: ¥5,100,000)
Fiscal Year 2003: ¥22,100,000 (Direct Cost: ¥17,000,000、Indirect Cost: ¥5,100,000)
Fiscal Year 2002: ¥23,400,000 (Direct Cost: ¥18,000,000、Indirect Cost: ¥5,400,000)
KeywordsCiguatoxin / Polyether / Ciguatera Poisoning / Total Synthesis / Immunoassay / Antibody / Neutralization of Toxicity / Sodium Channel / CTX1B / ビオチンコンジュゲート / 51-HydroxyCTX3C / エポキシ化 / 選択的酸化 / CTX3C / タンパク質コンジュゲート / ポリエーテル連結法
Research Abstract

Ciguatera poisoning is an important medical issue in the tropical and subtropical regions. The first total synthesis of ciguatoxin CTX3C, one of the causative toxins, through "unified convergent strategy, i.e., [X+2+Y] polyether assembly" was accomplished in 2001.
1.We then have developed the practical second-generation total synthesis of CTX3C.
2.Moreover, we have successfully applied it to synthesize 51-HydroxyCTX3C and CTX1B. Further methodological improvements allowed us to prepare a few mg of CTX3C and 51-HydroxyCTX3C, respectively, which be used for interdisciplinary researches.
3.Highly sensitive monoclonal antibody 8H2 was developed against CTX1B, 51-HydroxyCTX3C, and so on.
4.Sandwich Immunoassay using mAbs 8H2 and 10C9 was able to detect 51-HydroxyCTX at the level of pg/ml.
5.Sandwich immunoassay using mAbs 10C9 and 3D11 detected CTX3C in ciguateric fish caught in the Okinawa sea area.
6.Mice poisoned with CTX3C were cured by monoclonal antibodies we developed, which will be applied for humans. In addition, vaccines for ciguatera poisoning would be developed.
7.The central 9-membered F ring of ciguatoxins is proved to be crucial for their toxicity.
8.Synthetic ciguatoxins and bio-probes such as the conjugates with biotin will unveil the VSSC-ligand interaction at the atomic lebel and the gating mechanism.

Report

(6 results)
  • 2006 Annual Research Report   Final Research Report Summary
  • 2005 Annual Research Report
  • 2004 Annual Research Report
  • 2003 Annual Research Report
  • 2002 Annual Research Report
  • Research Products

    (177 results)

All 2007 2006 2005 2004 2003 2002 Other

All Journal Article (147 results) Book (1 results) Patent(Industrial Property Rights) (4 results) Publications (25 results)

  • [Journal Article] Convergent Synthesis of the ABCDE-Ring Fragment of the Caribbean Ciguatoxin C-CTX-1.2007

    • Author(s)
      M.Inoue
    • Journal Title

      Tetrahedron Lett. 48

      Pages: 2171-2175

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of the LMN-Ring Fragment of Caribbean Ciguatoxin.2007

    • Author(s)
      K.Yoshikawa
    • Journal Title

      Tetrahedron Lett. 48

      Pages: 2177-2180

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Convergent Synthesis of the ABCDE-Ring Fragment of the Caribbean Ciguatoxin C-CTX-1.2007

    • Author(s)
      M.Inoue, F.Saito, M.Iwatsu, Y.Ishihara, M.Hirama
    • Journal Title

      Tetrahedron Lett. 48

      Pages: 2171-2175

    • 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 LMN-Ring Fragment of Caribbean Ciguatoxin.2007

    • Author(s)
      K.Yoshikawa, M.Inoue, M.Hirama
    • Journal Title

      Tetrahedron Lett. 48

      Pages: 2177-2180

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Convergent Synthesis of the ABCDE-Ring Fragment of the Caribbean Ciguatoxin C-CTX-1.2007

    • Author(s)
      M.Inoue, et al.
    • Journal Title

      Tetrahedron Lett. 48

      Pages: 2171-2175

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Synthesis of the LMN-Ring Fragment of Caribbean Ciguatoxin.2007

    • Author(s)
      K.Yoshikawa, et al.
    • Journal Title

      Tetrahedron Lett. 48

      Pages: 2177-2180

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Formal Total Synthesis of Neocarzinostatin Chromophore.2006

    • Author(s)
      S.Kobayashi
    • Journal Title

      J. Org. Chem. 71

      Pages: 636-644

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Antitumor Enedyne Chromoprotein C-1027. Mechanistic Investigation of the Chromophore-Mediated Self-Decomposition Pathway.2006

    • Author(s)
      M.Inoue
    • Journal Title

      J. Am. Chem. Soc. 128

      Pages: 7896-7903

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Asymmetric Total Synthesis of (-)-Merrilactone A : Use of Bulky Protective Group as Long-Range Stereocontrolling Element.2006

    • Author(s)
      M.Inoue
    • Journal Title

      Angew. Chem. Int. Ed. 45

      Pages: 4843-4848

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Production of Monoclonal Antibodies for Sandwich Immunoassay Detection of 51-HydroxyCTX3C.2006

    • Author(s)
      T.Tsumuraya
    • Journal Title

      Toxicon 48

      Pages: 287-294

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Structural Factors Governing Stereoselective Heck Reaction for the Construction of the Oxindole Portion of TMC-95A.2006

    • Author(s)
      M.Inoue
    • Journal Title

      Synlett

      Pages: 3037-3040

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis and Evaluation of α-Helix Mimetics Based on a trans-Fused Polycyclic Ether : Sequence-Selective Binding to Aspartate Pairs in α-Helical Peptides.2006

    • Author(s)
      H.Oguri
    • Journal Title

      Tetrahedron Lett. 47

      Pages: 5801-5805

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Effect of Ciguatoxin 3C on Voltage-Gated Na^+ and K^+ Currents in Mouse Taste Cells.2006

    • Author(s)
      V.Ghiaroni
    • Journal Title

      Chem. Senses 31

      Pages: 673-680

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Total Synthesis of Ciguatoxin and 51-HydroxyCTX3C.2006

    • Author(s)
      M.Inoue
    • Journal Title

      J. Am. Chem. Soc. 128

      Pages: 9352-9354

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Direct Observation of ESR Spectra of Bicyclic Nine-Membered Enediynes at Ambient Temperature.2006

    • Author(s)
      M.Hirama
    • Journal Title

      Heterocycles 69

      Pages: 83-89

    • NAID

      40015163884

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Convergent Assembly of Polycyclic Ethers via Acyl Radical Addition to Unactivated Enol Ether.2006

    • Author(s)
      M.Inoue
    • Journal Title

      Org. Lett. 8

      Pages: 5801-5804

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Two Convergent Routes to the Left-Wing Fragment of Ciguatoxin CTX3C Using O,S-Acetals As Key Intermediates.2006

    • Author(s)
      M.Inoue
    • Journal Title

      Org. Lett. 8

      Pages: 5805-5808

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Formal Total Synthesis of Neocarzinostatin Chromophore.2006

    • Author(s)
      S.Kobayashi, M.Hori, G.X.Wang, M.Hirama
    • Journal Title

      J.Org.Chem. 71

      Pages: 636-644

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Antitumor Enedyne Chromoprotein C-1027. Mechanistic Investigation of the Chromophore-Mediated Self-Decomposition Pathway.2006

    • Author(s)
      M.Inoue, T.Usuki, N.Lee, M.Hirama, T.Tanaka, F.Hosoi, S.Ohie, T.Otani
    • Journal Title

      J.Am.Chem.Soc. 128

      Pages: 7896-7903

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Asymmetric Total Synthesis of (-)-Merrilactone A : Use of Bulky Protective Group as Long-Range Stereocontrolling Element.2006

    • Author(s)
      M.Inoue, T.Sato, M.Hirama
    • Journal Title

      Angew.Chem.Int.Ed. 45

      Pages: 4843-4848

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Production of Monoclonal Antibodies for Sandwich Immunoassay Detection of 51-HvdroxvCTX3C.2006

    • Author(s)
      T.Tsumuraya, I.Fujii, M.Inoue, A.Tatami, K.Miyazaki, M.Hirama
    • Journal Title

      Toxicon 48

      Pages: 287-294

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Structural Factors Governing Stereoselective Heck Reaction for the Construction of the Oxindole Portion of TMC-95A.2006

    • Author(s)
      M.Inoue, T.Takahashi, H.Furuyama, M.Hirama
    • Journal Title

      Synlett

      Pages: 3037-3040

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis and Evaluation of α-Helix Mimetics Based on a trans-Fused Polycyclic Ether : Sequence-Selective Binding to Aspartate Pairs in a-Helical Peptides.2006

    • Author(s)
      H.Oguri, S.Tanabe, A.Ohmura, M.Umetsu, M.Hirama
    • Journal Title

      Tetrahedron Lett 47

      Pages: 5801-5805

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Effect of Ciguatoxin 3C on Voltage-Gated Na^+ and K^+ Currents in Mouse Taste Cells.2006

    • Author(s)
      V.Ghiaroni, H.Fuwa, M.Inoue, M.Sasaki, K.Miyazaki, M.Hirama, T.Yasumoto, G.P.Rossini, G.Scalera, A.Bigiani
    • Journal Title

      Chem.Senses 31

      Pages: 673-680

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Total Synthesis of Ciguatoxin and 51-HvdroxvCTX3C.2006

    • Author(s)
      M.Inoue, K.Miyazaki, Y.Ishihara, A.Tatami, Y.Ohnuma, Y.Kawada, K.Komano, S.Yamashita, M.Hirama
    • Journal Title

      J.Am.Chem.Soc. 128

      Pages: 9352-9354

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Direct Observation of ESR Spectra of Bicyclic Nine-Membered Enediynes at Ambient Temperature.2006

    • Author(s)
      M.Hirama, K.Akiyama, P.Das, T.Mita, M.J.Lear, K.Iida, I.Sato, F.Yoshimura, T.Usuki, S.Tero-Kubota
    • Journal Title

      Heterocycles 69

      Pages: 83-89

    • NAID

      40015163884

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Convergent Assembly of Polycycyclic Ethers via Acyl Radical Addition to Unactivated Enol Ether.2006

    • Author(s)
      M.Inoue, Y.Ishihara, S.Yamashita, M.Hirama
    • Journal Title

      Org.Lett. 8

      Pages: 5801-5804

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Two Convergent Routes to the Left-Wing Fragment of Ciguatoxin CTX3C Using 0,S-Acetals As Key Intermediates.2006

    • Author(s)
      M.Inoue, S.Yamashita, Y.Ishihara, M.Hirama
    • Journal Title

      Org.Lett. 8

      Pages: 5805-5808

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Formal Total Synthesis of Neocarzinostatin Chromophore.2006

    • Author(s)
      S.Kobayashi, et al.
    • Journal Title

      J. Org. Chem. 71

      Pages: 636-644

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Antitumor Enedyne Chromoprotein C-1027. Mechanistic Investigation of the Chromophore-Mediated Self-Decomposition Pathway.2006

    • Author(s)
      M.Inoue, et al.
    • Journal Title

      J. Am. Chem. Soc. 128

      Pages: 7896-7903

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Asymmetric Total Synthesis of (-)-Merrilactone A : Use of Bulky Protective Group as Long-Range Stereocontrolling Element.2006

    • Author(s)
      M.Inoue, et al.
    • Journal Title

      Angew. Chem. Int. Ed. 45

      Pages: 4843-4848

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Production of Monoclonal Antibodies for Sandwich Immunoassay Detection of 51-HydroxyCTX3C.2006

    • Author(s)
      T.Tsumuraya, et al.
    • Journal Title

      Toxicon 48

      Pages: 287-294

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Structural Factors Governing Stereoselective Heck Reaction for the Construction of the Oxindole Portion of TMC-95A.2006

    • Author(s)
      M.Inoue, et al.
    • Journal Title

      Synlett

      Pages: 3037-3040

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Synthesis and Evaluation of α-Helix Mimetics Based on a trans-Fused Polycyclic Ether : Sequence-Selective Binding to Aspartate Pairs in α-Helical Peptides.2006

    • Author(s)
      H.Oguri, et al.
    • Journal Title

      Tetrahedron Lett. 47

      Pages: 5801-5805

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Effect of Ciguatoxin 3C on Voltage-Gated Na^+ and K^+ Currents in Mouse Taste Cells.2006

    • Author(s)
      V.Ghiaroni, et al.
    • Journal Title

      Chem. Senses 31

      Pages: 673-680

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Total Synthesis of Ciguatoxin and 51-HydroxyCTX3C.2006

    • Author(s)
      M.Inoue, et al.
    • Journal Title

      J. Am. Chem. Soc. 128

      Pages: 9352-9354

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Direct Observation of ESR Spectra of Bicyclic Nine-Membered Enediynes at Ambient Temperature.2006

    • Author(s)
      M.Hirama, et al.
    • Journal Title

      Heterocycles 69

      Pages: 83-89

    • NAID

      40015163884

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Convergent Assembly of Polycyclic Ethers via Acyl Radical Addition to Unactivated Enol Ether.2006

    • Author(s)
      M.Inoue, et al.
    • Journal Title

      Org. Lett. 8

      Pages: 5801-5804

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Two Convergent Routes to the Left-Wing Fragment of Ciguatoxin CTX3C Using O, S-Acetals As Key Intermediates.2006

    • Author(s)
      M.Inoue, et al.
    • Journal Title

      Org. Lett. 8

      Pages: 5805-5808

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Total Synthesis of Ciguatoxin CTX3C: A Venture into the Problems of Ciguatera Seafood Poisoning.2006

    • Author(s)
      M.Hirama
    • Journal Title

      Chem.Rec., 5

      Pages: 240-250

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Efficient Construction of the Kedarcidin Chromophore Ansamacrolide.2005

    • Author(s)
      Y.Koyama
    • Journal Title

      Org. Lett. 6

      Pages: 267-270

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] ESR Studies on DNA Cleavage Induced by Enedyne C-1027 Chromophore.2005

    • Author(s)
      T.Usuki
    • Journal Title

      Bioorg. Med. Chem. 13

      Pages: 5218-5224

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Total Synthesis of Ciguatoxin CTX3C : A Venture into the Problems of Ciguatera Seafood Poisoning.2005

    • Author(s)
      M.Hirama
    • Journal Title

      Chem. Rec. 5

      Pages: 240-250

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Convergent Strategies for Syntheses of trans-Fused Polycyclic Ethers.2005

    • Author(s)
      M.Inoue
    • Journal Title

      Chem. Rev. 105

      Pages: 4379-4405

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Efficient Construction of the Kedarcidin Chromophore Ansamacrolide.2005

    • Author(s)
      Y.Koyama, M.J.Lear, F.Yoshimura, I.Ohashi, T.Mashimo, M.Hirama
    • Journal Title

      Org.Lett. 6

      Pages: 267-270

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] ESR Studies on DNA Cleavage Induced by Enedyne C-1027 Chromophore.2005

    • Author(s)
      T.Usuki, M.Inoue, K.Akiyama, M.Hirama
    • Journal Title

      Bioorg.Med.Chem. 13

      Pages: 5218-5224

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Total Synthesis of Ciguatoxin CTX3C : A Venture into the Problems of Ciguatera Seafood Poisoning.2005

    • Author(s)
      M.Hirama
    • Journal Title

      Chem.Rec 5

      Pages: 240-250

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Convergent Strategies for Syntheses of trans-Fused Polycyclic Ethers.2005

    • Author(s)
      M.Inoue
    • Journal Title

      Chem.Rev. 105

      Pages: 4379-4405

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary 2005 Annual Research Report
  • [Journal Article] Efficient Construction of the Kedarcidin Chromophore Ansamacrolide.2005

    • Author(s)
      Y.Koyama et al.
    • Journal Title

      Org.Lett., 6

      Pages: 267-270

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Design and Synthesis of a trans-Fused Polycyclic Ether Skeleton as an α-Helix Mimetic Scaffold.2005

    • Author(s)
      H.Oguri et al.
    • Journal Title

      Tetrahedron Lett., 46

      Pages: 2179-2183

    • Related Report
      2005 Annual Research Report
  • [Journal Article] ESR Studies on DNA Cleavage Induced by Enedyne C-1027 Chromophore.2005

    • Author(s)
      T.Usuki et al.
    • Journal Title

      Bioorg.Med.Chem., 13

      Pages: 5218-5224

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Formal Total Synthesis of Neocarzinostatin Chromophore.2005

    • Author(s)
      S.Kobayashi et al.
    • Journal Title

      J.Org.Chem., 71

      Pages: 636-644

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Glycoglycerolipid from the Membranes of Acholeplasma laidlaw ii Binds to Human Immunodeficiency Virus-1(HIV-1) and Accel erates Its Entry into Cells.2004

    • Author(s)
      T.Shimizu
    • Journal Title

      Current Microbiology 48

      Pages: 182-188

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] TMC-95A, a Reversible Proteasome Inhibitor, Induces Neurite Outgrowth in PC12 Cells.2004

    • Author(s)
      M.Inoue
    • Journal Title

      Bioorg. Med. Chem. Lett. 14

      Pages: 663-665

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Rational Design of a Supra C-1027 : Kinetically Stabilized Analogue of the Antitumor Enediyne Chromoprotein.2004

    • Author(s)
      T.Usuki
    • Journal Title

      J. Am. Chem. Soc. 126

      Pages: 3022-3023

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Convergent Approach to the Maduropeptin Chromophore : Aryl Ether Formation of (R)-3-Aryl-3-hydroxypropanamide and Cyclization of Macrolactam.2004

    • Author(s)
      N.Kato
    • Journal Title

      Tetrahedron 60

      Pages: 3161-3172

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Use of Polystyrene-Supported DBU in the Synthesis and α -Selective Glycosylation Study of the Unstable Schmidt Donor of L-Kedarosamine.2004

    • Author(s)
      I.Ohashi
    • Journal Title

      Org. Lett. 6

      Pages: 719-722

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis and Preliminary Biological Evaluation of Truncated Zoanthenol Analogues.2004

    • Author(s)
      G.Hirai
    • Journal Title

      Bioorg. Med. Chem. Lett. 14

      Pages: 2647-2651

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] A New Stereoselective Synthesis of Ciguatoxin Right Wing Fragments.2004

    • Author(s)
      M.Inoue
    • Journal Title

      J. Org. Chem. 69

      Pages: 2797-2804

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] A Quantitative and Comparative Study of the Effects of a Synthetic Ciguatoxin CTX3C on the Kinetic Properties of Voltage-Dependent Sodium Channels.2004

    • Author(s)
      K.Yamaoka
    • Journal Title

      Br. J. Pharmacol 142

      Pages: 879-889

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] First and Second Generation Total Synthesis of Ciguatoxin CTX3C.2004

    • Author(s)
      M.Inoue
    • Journal Title

      Proc. Natl. Acad. Sci. USA 101

      Pages: 12013-12018

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Spin-Trapping of ^<13>C-Labeled p-Benzynes, Generated via the Masamune-Bergman Cyclization of Bicyclic Nine-Membered Enediynes.2004

    • Author(s)
      T.Usuki
    • Journal Title

      Angew. Chem. Int. Ed. 43

      Pages: 5249-5253

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of the Fully Functionalized Nine-Membered Diyne Core of the C-1027 Chromophore.2004

    • Author(s)
      M.Inoue
    • Journal Title

      Tetrahedron Lett. 45

      Pages: 6439-6442

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Stereocontrolled Synthesis of the ABCDE Ring Moiety of Ciguatoxin CTX3C.2004

    • Author(s)
      S.Kobayashi
    • Journal Title

      Tetrahedron 60

      Pages: 8375-8396

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of the Bicyclic [7.3.0] Enediyne System of the Maduropeptin Chromophore : Remarkable Atropisomerism of Ansamacrolactam and Isomerization of the C4-C13 Double Bond.2004

    • Author(s)
      N.Kato
    • Journal Title

      Synlett

      Pages: 2107-2110

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of the Bicyclo[7.3.0]dodecatrienediyne Core of the C-1027 Chromophore.2004

    • Author(s)
      M.Inoue
    • Journal Title

      Org. Lett. 6

      Pages: 3833-3836

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of the C-1027 Chromophore Framework through Atropselective Macrolactonization.2004

    • Author(s)
      M.Inoue
    • Journal Title

      Angew. Chem. Int. Ed. 43

      Pages: 6500-6505

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] A Formal Total Synthesis of (+)-Pinnatoxin A.2004

    • Author(s)
      S.Sakamoto
    • Journal Title

      Angew. Chem. Int. Ed. 43

      Pages: 6505-6510

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Total Synthesis of Ciguatoxin CTX3C, a Causative Toxin of Ciguatera Seafood Poisoning.2004

    • Author(s)
      M.Inoue
    • Journal Title

      Synlett 4

      Pages: 577-595

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] 9員環エンジイン抗生物質N1999-A2の全合成 : 絶対配置とDNA切断2004

    • Author(s)
      小林正治
    • Journal Title

      有機合成化学協会誌 62

      Pages: 184-193

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] シガトキシン全合成2004

    • Author(s)
      平問正博
    • Journal Title

      Aoba Scientia 3

      Pages: 2-3

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Evolution of a Practical Total Synthesis of Ciguatoxin CTX3C.2004

    • Author(s)
      M.Inoue
    • Journal Title

      Acc. Chem. Res. 37

      Pages: 961-968

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Glycoglycerolipid from the Membranes of Acholeplasma laidlawii Binds to Human Immunodeficiency Virus-1(HIV-1) and Accelerates Its Entry into Cells.2004

    • Author(s)
      T.Shimizu, S.Arai, H.Imai, T.Oishi, M.Hirama, A.Koito, Y.Kida, K.Kuwano
    • Journal Title

      Current Microbiology 48

      Pages: 182-188

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] TMC-95A, a Reversible Proteasome Inhibitor, Induces Neurite Outgrowth in PC12 Cells.2004

    • Author(s)
      M.Inoue, H.Zhai, H.Sakazaki, H.Furuyama, Y.Fukuyama, M.Hirama
    • Journal Title

      Bioorg.Med.Chem.Lett. 14

      Pages: 663-665

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Rational Design of a Supra C-1027 : Kinetically Stabilized Analogue of the Antitumor Enediyne Chromoprotein.2004

    • Author(s)
      T.Usuki, M.Inoue, M.Hirama, T.Tanaka
    • Journal Title

      J.Am.Chem.Soc. 126

      Pages: 3022-3023

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Convergent Approach to the Maduropeptin Chromophore : Aryl Ether Formation of (R)-3-Aryl-3-hydroxypropanamide and Cyclization of Macrolactam.2004

    • Author(s)
      N.Kato, S.Shimamura, S.Khan, F.Takeda, Y.Kikai, M.Hirama
    • Journal Title

      Tetrahedron 60

      Pages: 3161-3172

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Use of Polystyrene-Supported DBU in the Synthesis and a-Selective Glycosylation Study of the Unstable Schmidt Donor of L-Kedarosamine.2004

    • Author(s)
      I.Ohashi, M.J.Lear, F.Yoshimura, M.Hirama
    • Journal Title

      Org.Lett. 6

      Pages: 719-722

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis and Preliminary Biological Evaluation of Truncated Zoanthenol Analogues.2004

    • Author(s)
      G.Hirai, H.Oguri, M.Hayashi, K.Koyama, Y.Koizumi, S.M.Moharram, M.Hirama
    • Journal Title

      Bioorg.Med.Chem.Lett. 14

      Pages: 2647-2651

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] A New Stereoselective Synthesis of Ciguatoxin Right Wing Fragments.2004

    • Author(s)
      M.Inoue, S.Yamashita, A.Tatami, K.Miyazaki, M.Hirama
    • Journal Title

      J.Org.Chem. 69

      Pages: 2797-2804

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] A Quantitative and Comparative Study of the Effects of a Synthetic Ciguatoxin CTX3C on the Kinetic Properties of Voltage-Dependent Sodium Channels.2004

    • Author(s)
      K.Yamaoka, M.Inoue, H.Miyahara, K.Miyazaki, M.Hirama
    • Journal Title

      Br.J.Pharmacol. 142

      Pages: 879-889

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] First and Second Generation Total Synthesis of Ciguatoxin CTX3C.2004

    • Author(s)
      M.Inoue, K.Miyazaki, H.Uehara, M.Maruyama, M.Hirama
    • Journal Title

      Proc.Natl.Acad.Sci.USA 101

      Pages: 12013-12018

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Spin-Trapping of ^<13>C-Labeled p-Benzynes, Generated via the Masamune-Bergman Cyclization of Bicyclic Nine-Membered Enediynes.2004

    • Author(s)
      T.Usuki, T.Mita, M.J.Lear, P.Das, F.Yoshimura, M.Inoue, M.Hirama, K.Akiyama, S.Tero-Kubota
    • Journal Title

      Angew.Chem.Int.Ed. 43

      Pages: 5249-5253

    • 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 Fully Functionalized Nine-Membered Diyne Core of the C-1027 Chromophore.2004

    • Author(s)
      M.Inoue, T.Kikuchi, M.Hirama
    • Journal Title

      Tetrahedron Lett. 45

      Pages: 6439-6442

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Stereocontrolled Synthesis of the ABCDE Ring Moiety of Ciguatoxin CTX3C.2004

    • Author(s)
      S.Kobayashi, Y.Takahashi, K.Komano, B.H.Alizadeh, Y.Kawada, T.Oishi, S.Tanaka, Y.Ogasawara, S.Sasaki, M.Hirama
    • Journal Title

      Tetrahedron 60

      Pages: 8375-8396

    • 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 Bicyclic [7.3.0] Enediyne System of the Maduropeptin Chromophore : Remarkable Atropisomerism of Ansamacrolactam and Isomerization of the C4-C13 Double Bond.2004

    • Author(s)
      N.Kato, S.Shimamura, Y.Kikai, M.Hirama
    • Journal Title

      Synlett

      Pages: 2107-2110

    • 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 Bicyclo[7.3.0]dodecatrienediyne Core of the C-1027 Chromophore.2004

    • Author(s)
      M.Inoue, S.Hatano, M.Kodama, T.Sasaki, T.Kikuchi, M.Hirama
    • Journal Title

      Org.Lett. 6

      Pages: 3833-3836

    • 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 C-1027 Chromophore Framework through Atropselective Macrolactonization.2004

    • Author(s)
      M.Inoue, T.Sasaki, S.Hatano, M.Hirama
    • Journal Title

      Angew.Chem.Int.Ed. 43

      Pages: 6500-6505

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Formal Total Synthesis of (+)-Pinnatoxin A.2004

    • Author(s)
      S.Sakamoto, H.Sakazaki, K.Hagiwara, K.Kamada, K.Ishii, T.Noda, M.Inoue, M.Hirama
    • Journal Title

      Angew.Chem.Int.Ed. 43

      Pages: 6505-6510

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Total Synthesis of Ciguatoxin CTX3C, a Causative Toxin of Ciguatera Seafood Poisoning.2004

    • Author(s)
      M.Inoue, M.Hirama
    • Journal Title

      Synlett 4

      Pages: 577-595

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Evolution of a Practical Total Synthesis of Ciguatoxin CTX3C.2004

    • Author(s)
      M.Inoue, M.Hirama
    • Journal Title

      Acc.Chem.Res. 37

      Pages: 961-968

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Glycoglycerolipid from the Membranes of Acholeplasma laidlawii Binds to Human Immunodeficiency Virus-1(HIV-1) and Accelerates Its Entry into Cells2004

    • Author(s)
      T.Shimizu, S.Arai, H.Imai, T.Oishi, M.Hirama, A.Koito, Y.Kida, K.Kuwano
    • Journal Title

      Current Microbiology 48

      Pages: 182-188

    • Related Report
      2004 Annual Research Report
  • [Journal Article] TMC-95A, a Reversible Proteasome Inhibitor, Induces Neurite Outgrowth in PC12 Cells2004

    • Author(s)
      M.Inoue, H.Zhai, H.Sakazaki, H.Furuyama, Y.Fukuyama, M.Hirama
    • Journal Title

      Bioorg.Med.Chem.Lett. 14

      Pages: 663-665

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Rational Design of a Supra C-1027 : Kinetically Stabilized Analogue of the Antitumor Enediyne Chromoprotein2004

    • Author(s)
      T.Usuki, M.Inoue, M.Hirama, T.Tanaka
    • Journal Title

      Bioorg.Med.Chem.Lett. 14

      Pages: 663-665

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Convergent Approach to the Maduropeptin Chromophore : Aryl Ether Formation of (R)-3-Aryl-3-hydroxypropanamide and Cyclization of Macrolactam2004

    • Author(s)
      N.Kato, S.Shimamura, S.Khan, F.Takeda, Y.Kikai, M.Hirama
    • Journal Title

      Tetrahedron 60

      Pages: 3161-3172

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Use of Polystyrene-Supported DBU in the Synthesis and α-Selective Glycosylation Study of the Unstable Schmidt Donor of L-Kedarosamine2004

    • Author(s)
      I.Ohashi, M.J.Lear, F.Yoshimura, M.Hirama
    • Journal Title

      Tetrahedron Lett. 45

      Pages: 2053-5056

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Synthesis and Preliminary Biological Evaluation of Truncated Zoanthenol Analogues2004

    • Author(s)
      G.Hirai, H.Oguri, M.Hayashi, K.Koyama, Y.Koizumi, S.M.Moharram, M.Hirama
    • Journal Title

      Bioorg.Med.Chem.Lett. 14

      Pages: 2647-2651

    • Related Report
      2004 Annual Research Report
  • [Journal Article] A New Stereoselective Synthesis of Ciguatoxin Right Wing Fragments2004

    • Author(s)
      M.Inoue, S.Yamashita, A.Tatami, K.Miyazaki, M.Hirama
    • Journal Title

      J.Org.Chem. 69

      Pages: 2797-2804

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Phage-Display Selection of Antibodies to the Left End of CTX3C Using Synthetic Fragments2004

    • Author(s)
      Y.Nagumo, H.Ouri, K.Tsumoto, Y.Shindo, M.Hirama, T.Tsumuraya, I.Fuji, Y.Tomioka, M.Mizugaki, I.Kumagai
    • Journal Title

      J.Immunol.Methods 289

      Pages: 137-146

    • Related Report
      2004 Annual Research Report
  • [Journal Article] A Quantitative and Comparative Study of the Effects of a Synthetic Ciguatoxin CTX3C on the Kinetic Properties of Voltage-Dependent Sodium Channels2004

    • Author(s)
      K.Yamaoka, M.Inoue, H.Miyahara, K.Miyazaki, M.Hirama
    • Journal Title

      Br.J.Pharmacol 142

      Pages: 879-889

    • Related Report
      2004 Annual Research Report
  • [Journal Article] First and Second Generation Total Synthesis of Ciguatoxin CTX3C2004

    • Author(s)
      M.Inoue, K.Miyazaki, H.Uehara, M.Maruyama, M.Hirama
    • Journal Title

      Proc.Natl.Acad.Sci.USA 101

      Pages: 12013-12018

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Spin-Trapping of ^<13>C-Labeled p-Benzynes, Generated via the Masamune-Bergman Cyclization of Bicyclic Nine-Membered Enediynes2004

    • Author(s)
      T.Usuki, T.Mita, M.J.Lear, P.Das, F.Yoshimura, M.Inoue, M.Hirama, K.Akiyama, S.Tero-Kubota
    • Journal Title

      Angew.Chem.Int.Ed. 43

      Pages: 5249-5253

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Synthesis of the Fully Functionalized Nine-Membered Diyne Core of the C-1027 Chromophore2004

    • Author(s)
      M.Inoue, T.Kikuchi, M.Hirama
    • Journal Title

      Tetrahedron Lett. 45

      Pages: 6439-6442

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Stereocontrolled Synthesis of the ABCDE Ring Moiety of Ciguatoxin CTX3C2004

    • Author(s)
      S.Kobayashi, Y.Takahashi, K.Komano, B.H.Alizadeh, Y.Kawada, T.Oishi
    • Journal Title

      Tetrahedron 60

      Pages: 8375-8396

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Synthesis of the Bicyclic[7:3.0] Enediyne System of the Maduropeptin Chromophore : Remarkable Atropisomerism of Ansamacrolactam and Isomerization of the C4-C13 Double Bond2004

    • Author(s)
      N.Kato, S.Shimamura, Y.Kikai, M.Hirama
    • Journal Title

      Synlett

      Pages: 2107-2110

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Synthesis of the Bicyclo[7.3.0]dodecatrienediyne Core of the C-1027 Chromophore2004

    • Author(s)
      M.Inoue, S.Hatano, M.Kodama, T.Sasaki, T.Kikuchi, M.Hirama
    • Journal Title

      Org.Lett. 6

      Pages: 3833-3836

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Synthesis of the C-1027 Chromophore Framework through Atropselective Macrolactonization2004

    • Author(s)
      M.Inoue, T.Sasaki, S.Hatano, M.Hirama
    • Journal Title

      Angew.Chem.Int.Ed. 43

      Pages: 6500-6505

    • Related Report
      2004 Annual Research Report
  • [Journal Article] A Formal Total Synthesis of (+)-Pinnatoxin A2004

    • Author(s)
      S.Sakamoto, H.Sakazaki, K.Hagiwara, K.Kamada, K.Ishii, T.Noda, M.Inoue, M.Hirama
    • Journal Title

      Angew.Chem.Int.Ed. 43

      Pages: 6505-6510

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Total Synthesis of Ciguatoxin CTX3C, a Causative Toxin of Ciguatera Seafood Poisoning2004

    • Author(s)
      M.Inoue, M.Hirama
    • Journal Title

      Synlett 4

      Pages: 577-595

    • Related Report
      2004 Annual Research Report
  • [Journal Article] 9員環エンジイン抗生物N1999-A2の全合成:絶対配置とDNA切断2004

    • Author(s)
      小林正治, 平間正博
    • Journal Title

      有機合成化学協会誌 62

      Pages: 184-193

    • Related Report
      2004 Annual Research Report
  • [Journal Article] シガトキシン全合成2004

    • Author(s)
      平間正博
    • Journal Title

      Aoba Scientia 3

      Pages: 2-3

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Evolution of a Practical Total Synthesis of Ciguatoxin CTX3C2004

    • Author(s)
      M.Inoue, M.Hirama
    • Journal Title

      Acc.Chem.Res. 37

      Pages: 961-968

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Inhibition of Brevetoxin Binding to the Voltage-gated Sodium Channel by Gambierol and Gambieric Acid-A2003

    • Author(s)
      M.Inoue
    • Journal Title

      Toxicon 41(4)

      Pages: 469-474

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] A Novel Route to 1, 8-Dihydroxynaphthalene-Derived Natural Products. Synthesis of (±)-CJ-12, 3722003

    • Author(s)
      M.Inoue
    • Journal Title

      Heterocycles 59

      Pages: 87-92

    • NAID

      40005626772

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Total Synthesis of TMC-95A2003

    • Author(s)
      M.Inoue
    • Journal Title

      Angew. Chem. Int. Ed. 42

      Pages: 2654-2657

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Construction of the AG-ring Unit of Pinnatoxin A via Intramolecular Alkylation and Aza-Wittig Reaction2003

    • Author(s)
      J.Wang
    • Journal Title

      Synlett

      Pages: 891-893

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Characterization of 11-Dehydro-Thromboxane B_2 Recombinant Antibody Obtained by Phage Display Technology2003

    • Author(s)
      L.-R.Thuruta
    • Journal Title

      Prostaglandins, Leukotrienes and Essential Fatty Acids 68

      Pages: 273-284

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis-Based Approach toward Direct Sandwich Immunoassay for Ciguatoxin CTX3C2003

    • Author(s)
      H.Ogur
    • Journal Title

      J. Am. Chem. Soc. 125

      Pages: 7608-7612

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] A Concise Route to the Right Wing of Ciguatoxin2003

    • Author(s)
      A.Tatami
    • Journal Title

      Tetrahedron Lett. 44

      Pages: 5229-5233

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Divergent Synthesis of the Tetracyclic Ethers of 6-X-7-6 Ring Systems.2003

    • Author(s)
      M.Inoue
    • Journal Title

      Tetrahedron 59

      Pages: 5645-5659

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Total Synthesis of Merrilactone A2003

    • Author(s)
      M.Inoue
    • Journal Title

      J. Am. Chem. Soc. 125

      Pages: 10772-10773

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] 最近の学界の話題-食中毒シガテラ毒素の全合成2003

    • Author(s)
      平間 正博
    • Journal Title

      青葉理学振興会報告 3

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] シガトキシンの全合成と抗体2003

    • Author(s)
      平間 正博
    • Journal Title

      CREST"単一分子・原子レベルの反応制御"領域ニュースレター 7

      Pages: 20-22

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] 海洋天然物の全合成2003

    • Author(s)
      平間 正博
    • Journal Title

      海洋天然物化学-化合物ライブラリーとしての評価(21世紀の化学の潮流を探る報告書No.16)(日本化学会)

      Pages: 21-26

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] 海洋天然物の全合成2003

    • Author(s)
      平間 正博
    • Journal Title

      先端化学シリーズV : 海洋天然物・錯体・コンビナトリアル(全合成日本化学会編)(丸善)

      Pages: 16-19

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] 「全合成」の現状と今後の展望2003

    • Author(s)
      平間 正博
    • Journal Title

      全合成-天然物から超タンパク質まで(21世紀の化学の潮流を探る報告書No.23)(日本化学会)

      Pages: 1-1

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] 全合成の現状と今後の展望2003

    • Author(s)
      平間 正博
    • Journal Title

      先端化学シリーズV : 海洋天然物・錯体・コンビナトリアル・全合成(日本化学会編)(丸善)

      Pages: 239-240

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Inhibition of Brevetoxin Binding to the Voltage-gated Sodium Channel by Gambierol and Gambieric Acid-A.2003

    • Author(s)
      M.Inoue, M.Hirama, M.Satake, K.Sugiyama, T.Yasumoto
    • Journal Title

      Toxicon 41(4)

      Pages: 469-474

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] A Novel Route to 1,8-Dihydroxynaphthalene-Derived Natural Products. Synthesis of (±)-CJ-12,372.2003

    • Author(s)
      M.Inoue, K.Nabatame, M.Hirama
    • Journal Title

      Heterocycles 59

      Pages: 87-92

    • NAID

      40005626772

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Total Synthesis of TMC-95A.2003

    • Author(s)
      M.Inoue, H.Sakazaki, H.Furuyama, M.Hirama
    • Journal Title

      Angew.Chem.Int.Ed. 42

      Pages: 2654-2657

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Construction of the AG-ring Unit of Pinnatoxin A via Intramolecular Alkylation and Aza-Wittig Reaction.2003

    • Author(s)
      J.Wang, S.Sakamoto, K.Kamata, A.Nitta, T.Noda, H.Oguri, M.Hirama
    • Journal Title

      Synlett

      Pages: 891-893

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Characterization of 11-Dehydro-Thromboxane B_2 Recombinant Antibody Obtained by Phage Display Technology.2003

    • Author(s)
      L.-R.Thuruta, Y.Tomioka, T.Hishinuma, Y.Kato, K.Itoh, T.Suzuki, H.Oguri, M.Hirama, J.Goto, M.Mizugaki
    • Journal Title

      Prostaglandins, Leukotrienes and Essential Fatty Acids 68

      Pages: 273-284

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis-Based Approach toward Direct Sandwich Immunoassay for Ciguatoxin CTX3C.2003

    • Author(s)
      H.Oguri, M.Hirama, T.Tsumuraya, I.Fujii, M.Maruyama, H.Uehara, Y.Nagumo
    • Journal Title

      J.Am.Chem.Soc. 125

      Pages: 7608-7612

    • NAID

      130006997539

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] A Concise Route to the Right Wing of Ciguatoxin.2003

    • Author(s)
      A.Tatami, M.Inoue, H.Uehara, M.Hirama
    • Journal Title

      Tetrahedron Lett. 44

      Pages: 5229-5233

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Divergent Synthesis of the Tetracyclic Ethers of 6-X-7-6 Ring Systems.2003

    • Author(s)
      M.Inoue, J.Wang, G.-X.Wang, Y.Ogasawara, M.Hirama
    • Journal Title

      Tetrahedron 59

      Pages: 5645-5659

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Total Synthesis of Merrilactone A.2003

    • Author(s)
      M.Inoue, T.Sato, M.Hirama
    • Journal Title

      J.Am.Chem.Soc. 125

      Pages: 10772-10773

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Convergent Synthesis of the ABCDE Ring System of Ciguatoxin CTX3C2002

    • Author(s)
      M.Maruyama
    • Journal Title

      Tetrahedron 58

      Pages: 1835-1851

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Convergent Synthesis of The HIJKLM Ring Fragment of Ciguatoxin CTX3C2002

    • Author(s)
      H.Uehara
    • Journal Title

      Tetrahedron 58

      Pages: 6493-6512

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Novel Assembly of Cyclic Ethers by Coupling α -Chlorosulfides and Alcohols.2002

    • Author(s)
      M.Inoue
    • Journal Title

      Organic Letters 4

      Pages: 3439-3442

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Practical Total Synthesis of Ciguatoxin CTX3C by Improved Protective Group Strategy2002

    • Author(s)
      M.Inoue
    • Journal Title

      Organic Letters 4

      Pages: 4551-4554

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] シガトキシン全合成への道のり2002

    • Author(s)
      平間 正博
    • Journal Title

      現代化学 373

      Pages: 55-62

    • NAID

      40001096487

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] フグ毒よりコワーイ食中毒シガテラ-毒素の全合成から予防へ2002

    • Author(s)
      平間 正博
    • Journal Title

      化学と教育(日本化学会) 50(6)

      Pages: 443-445

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] 毒素CTX3Cの化学合成から予防へ-世界最大規模の海産物食中毒シガテラ2002

    • Author(s)
      平間 正博
    • Journal Title

      化学と工業 55(7)

      Pages: 786-789

    • NAID

      10009483478

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] 食中毒(シガテラ中毒)の原因毒シガトキシンCTX3Cの化学合成2002

    • Author(s)
      平間 正博
    • Journal Title

      Medical Science Digest 28(9)

      Pages: 398-399

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Convergent Synthesis of the ABCDE Ring System of Ciguatoxin CTX3C.2002

    • Author(s)
      M.Maruyama, M.Inoue, T.Oishi, H.Oguri, Y.Ogasawara, Y.Shindo, M.Hirama
    • Journal Title

      Tetrahedron 58(Symposia in Print)

      Pages: 1835-1851

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Convergent Synthesis of The HIJKLM Ring Fragment of Ciguatoxin CTX3C.2002

    • Author(s)
      H.Uehara, T.Oishi, M.Inoue, M.Shoji, Y.Nagumo, M.Kosaka, J.-Y.Le Brazidec, M.Hirama
    • Journal Title

      Tetrahedron 58

      Pages: 6493-6512

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Novel Assembly of Cyclic Ethers by Coupling α-Chlorosulfides and Alcohols.2002

    • Author(s)
      M.Inoue, G.X.Wang, J.Wang, M.Hirama
    • Journal Title

      Org.Lett. 4

      Pages: 3439-3442

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Practical Total Synthesis of Ciguatoxin CTX3C by Improved Protective Group Strategy.2002

    • Author(s)
      M.Inoue, H.Uehara, M.Maruyama, M.Hirama
    • Journal Title

      Org.Lett. 4

      Pages: 4551-4554

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Book] My Favorite Organic Synthesis2002

    • Author(s)
      M.Hirama
    • Total Pages
      253
    • Publisher
      有機合成化学協会
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Patent(Industrial Property Rights)] シガトキシンCTX1B類の合成方法及びシガトキシンCTX1B類の合成に有用な化合物類2006

    • Inventor(s)
      平間正博, 井上将行
    • Industrial Property Rights Holder
      (独)科学技術振興機構
    • Industrial Property Number
      2006-011267
    • Filing Date
      2006-01-19
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Patent(Industrial Property Rights)] シガトキシンCTX1B類の合成方法及びシガトキシンCTX1B類の合成に有用な化合物類2006

    • Inventor(s)
      平間 正博, 井上 将行
    • Industrial Property Rights Holder
      独)科学技術振興機構
    • Industrial Property Number
      2006-011267
    • Filing Date
      2006-01-19
    • Related Report
      2005 Annual Research Report
  • [Patent(Industrial Property Rights)] シガトキシン類を認識するモノクローナル抗体、およびそれを用いるシガトキシン類検出キット2005

    • Inventor(s)
      藤井郁雄, 円谷健, 平間正博, 井上将行
    • Industrial Property Rights Holder
      大阪府
    • Industrial Property Number
      2005-008132
    • Filing Date
      2005-01-14
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Patent(Industrial Property Rights)] シガトキシン類を認識するモノクローナル抗体、およびそれを用いるシガトキシン類検出キット2005

    • Inventor(s)
      藤井 郁雄, 円谷 健, 平間 正博, 井上 将行
    • Industrial Property Rights Holder
      大阪府
    • Industrial Property Number
      2005-008132
    • Filing Date
      2005-01-14
    • Related Report
      2005 Annual Research Report
  • [Publications] M.Inoue, M.Hirata., M.Satake, K.Sugiyama, T.Yasumoto: "Inhibition of Brevetoxin Binding to the Voltage-gated Sodium Channel by Gambierol and Gambieric Acid-A"Toxicon. 41(4). 469-474 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Inoue, K.Nabatame, M.Hirama: "A Novel Route to 1, 8-Dihydroxynaphthalene-Derived Natural Products. Synthesis of (±)-CJ-12, 372"Heterocycles. 59. 87-92 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Inoue, H.Sakazaki, H.Furuyama, M.Hirama: "Total Synthesis of TMC-95A"Angew.Chem.Int.Ed.. 42. 2654-2657 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] J.Wang, S.Sakamoto, K.Kamata, A.Nitta, T.Noda, H.Oguri, M.Hirama: "Construction of the AG-ring Unit of Pinnatoxin A via Intramolecular Alkylation and Aza-Wittig Reaction"Synlett. 891-893 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] L.-R.Thuruta, Y.Tomioka, T.Hishinuma, Y.Kato, K.Itoh, T.Suzuki, H.Oguri, M.Hirama, J.Goto, M.Mizugaki: "Characterization of 11-Dehydro-Thromboxane B_2 Recombinant Antibody Obtained by Phage Display Technology"Prostaglandins, Leukotrienes and Essential Fatty Acids. 68. 273-284 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] H.Oguri, M.Hirama, T.Tsumuraya, I.Fujii, M.Maruyama, H.Uehara, Y.Nagumo: "Synthesis-Based Approach toward Direct Sandwich Immunoassay for Ciguatoxin CTX3C"J.Am.Chem.Soc.. 125. 7608-7612 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] A.Tatami, M.Inoue, H.Uehara, M.Hirama: "A Concise Route to the Right Wing of Ciguatoxin"Tetrahedron Lett.. 44. 5229-5233 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Inoue, J.Wang, G.-X.Wang, Y.Ogasawara, M.Hirama: "Divergent Synthesis of the Tetracyclic Ethers of 6-X-7-6 Ring Systems"Tetrahedron. 59. 5645-5659 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Inoue, T.Sato, M.Hirama: "Total Synthesis of Merrilactone A"J.Am.Chem.Soc.. 125. 10772-10773 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] T.Shimizu, S.Arai, H.Imai, T.Oishi, M.Hirama, A.Koito, Y.Kida.K.Kuwano: "Glycoglycerolipid from the Membranes of Acholeplasma laidlawii Binds to Human Immunodeficiency Virus-1(HIV-1) and Accelerates Its Entry into Cells"Current Microbiology. (in press).

    • Related Report
      2003 Annual Research Report
  • [Publications] 平間 正博: "最近の学界の話題-食中毒シガテラ毒素の全合成"青葉理学振興会報告. 3. (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] 平間 正博: "シガトキシンの全合成と抗体"CREST"単一分子・原子レベルの反応制御"領域ニュースレター. 7. 20-22 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] 平間 正博: "海洋天然物の全合成"21世紀の化学の潮流を探る報告書No.16「海洋天然物化学-化合物ライブラリーとしての評価」、日本化学会. 21-26 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] 平間 正博: "海洋天然物の全合成"先端化学シリーズV :海洋天然物・錯体・コンビナトリアル・全合成日本化学会編、丸善. 16-19 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] 平間 正博: "「全合成」の現状と今後の展望"21世紀の化学の潮流を探る報告書No.23「全合成-天然物から超タンパク質まで」、日本化学会. 1 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] 平間 正博: "全合成の現状と今後の展望"先端化学シリーズV:海洋天然物・錯体・コンビナトリアル・全合成、日本化学会編、丸善. 239-240 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Maruyama, M.Inoue, T.Oishi, R.Oguri, Y.Ogasawara, Y.Shindo, M.Hirama: "Convergent Synthesis of the ABCDE Ring System of Ciguatoxin CTX3C"Tetrahedron. 58. 1835-1851 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] H.Uehara, T.Oishi, M.Inoue, M.Shoji, Y.Nagumo, M.Kosaka, J.-Y.Le Brazidec, M.Hirama: "Convergent Synthesis of The HIJKLM Ring Fragment of Ciguatoxin CTX3C"Tetrahedron. 58. 6493-6512 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.Inoue, G.X.Wang, J.Wang, M.Hirama: "Novel Assembly of Cyclic Ethers by Coupling α-Chlorosulfides and Alcohols"Organic Letters. 4. 3439-3442 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.Inoue, H.Uehara, M.Maruyama, M.Hirama: "Practical Total Synthesis of Ciguatoxin CTX3C by Improved Protective Group Strategy"Organic Letters. 4. 4551-4554 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] 平間 正博, 大石 徹: "シガトキシン全合成への道のり"現代化学. 373. 55-62 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] 平間 正博: "フグ毒よりコワーイ食中毒シガテラ-毒素の全合成から予防へ"化学と教育(日本化学会). 50(6). 443-445 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] 平間 正博, 大石 徹: "毒素CTX3Cの化学合成から予防へ-世界最大規模の海産物食中毒シガテラ"化学と工業. 55(7). 786-789 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] 平間 正博: "食中毒(シガテラ中毒)の原因毒シガトキシンCTX3Cの化学合成"Medical Science Digest. 28(9). 398-399 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.Hirama, T.Oishi 他: "My Favorite Organic Synthesis"有機合成化学協会. 253 (2002)

    • Related Report
      2002 Annual Research Report

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

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