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Biological and Organic Chemical Investigation on Blepharismins and Their Related Natural Products

Research Project

Project/Area Number 10480151
Research Category

Grant-in-Aid for Scientific Research (B).

Allocation TypeSingle-year Grants
Section一般
Research Field Bioorganic chemistry
Research InstitutionKochi University

Principal Investigator

KOTSUKI Hiyoshizo  Kochi University, Faculty of Science, Department of Materials Science, Professor, 理学部, 教授 (80093954)

Co-Investigator(Kenkyū-buntansha) MATSUOKA Tatsuomi  Kochi University, Faculty of Science, Department of Natural Science, Professor, 理学部, 教授 (90209510)
Project Period (FY) 1998 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥13,100,000 (Direct Cost: ¥13,100,000)
Fiscal Year 2000: ¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1999: ¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 1998: ¥7,500,000 (Direct Cost: ¥7,500,000)
KeywordsBlepharismins / Aromatic Alkylation / Anthraquinone Structures / Oxidative Coupling / Photosignaling / Stentorins / Hypericin / Photosensory Transduction / アントラキノン / ヒペリミン / Friedel-Craftsアルキル化 / アントロン / 光シグナル / 光センサー複合体 / Sc(OTf)3 / 分子内Friedel-Craftsアシル化 / ジフェニール骨格
Research Abstract

(a) Structural Study of Blepharismins and Their Related Natural Pigments : Computer-aided analysis of blepharismins, stentorins, and hypericin has been performed and their three-dimensional structures having the "propeller" butterfly-like conformation have been clarified.
(b) Synthetic Study of Blepharismins and Their Related Natural Pigments :
-1. New Method for Aromatic Alkylation : To introduce an alkyl side chain on an aromatic ring, we developed the following two methods : (a) Friedel-Crfats-type alkylation using secondary alcohol methanesulfonates as an electrophile in the presence of a catalytic amount of Sc(OTf)_3 or TfOH ; (b) Regioselective nucleophilic aromatic substitution using Grignard reagents upon o- or p-methoxy-substituted aromatic carboxylates.
-2. Synthesis of Anthraquinone Key Skeletons : The anthraquinone key component of blepharismin-3 and stentorin-C was prepared by treatment of benzoic acid derivatives with (CF_3CO)_2O via intramolecular Friedel-Crafts acylation f … More ollowed by oxidation in the air.
-3. High-Pressure Promoted Construction of Biphenol Key Skeleton : High-pressure promoted condensation between phenols and aromatic aldehydes was efficiently proceeded in the presence of a catalytic amount of TfOH to produce the desired biphenol key skeleton of blepharismins.
-4. Synthesis of Perylene Quinone Structure : Intramolecular oxidative coupling of biphenol derivatives has been achieved by using the Koga' reagent (CuCl(OH)・
TMEDA complex) in giving the perilene quinone structure of blepharismins.
(c) Structure of Photosensory Complex : Spectroscopic analysis of free pigment
(blepharismin) and pigment (blepharismin)/protein complex, analysis of pigment contents bound to the protein or observation of photosensory organelle suggested that a large number of free pigment molecules are regularly arranged in vivo. This crystal -like structure may function as light-harvesting antenna for activating reaction center blepharismin/200 kD protein
complex.
(d) Photosensory Transduction : Analyses of molecular structure of light-irradiated blepharismin suggested that light-induced dissociation of phenol group (side chain) is not
involved in activation of photosensory transduction chain. Spectroscopic analysis of photoreceptor complex indicated that active oxygen produced by photosensitization of light-activated blepharismin or energy or electron transfer from first excited singlet of pigment would be involved in activation of photosensory transduction chain.
(e) Singaling Mechanism between Photoreceptor Organelle and Cell Membrane : We revealed that photosignal is finally transduced into H+ signal ; H+ is released from outer membrane of photoreceptor organelle so that evoked depolarization of cell membrane. Less

Report

(4 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • 1998 Annual Research Report
  • Research Products

    (94 results)

All Other

All Publications (94 results)

  • [Publications] H.Kotsuki, 他3名: "Solvent-Free Organic Reactions on Silica Gel Supports, Facile Transformation of Epoxides to β-Halohydrins with Lithium Halides "Tetrahedron. 54. 2709-2722 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki, 他3名: "A Facile New Method for Selective Doprotection of N-(tort-Butoxycarbonyl)-Protected Carboxamids with Yb(OTt)_3 Supported on Silica Gel"Tetrahedron Letters. 39. 4869-4870 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki, 他2名: "Scandium (III) Trifluoromethanesulfonate-Catalyzed Friedel-Crafts Alkylation of Aromatic Compounds with Secondary-Alcohol Methanesulfonates"Synlett. 255-256 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki: "Organic Synthesis at High Pressure.Efficient Ring Opening Reaction of Epoxides with Heterocycles"Review of High Pressure Science & Technology. 7. 1250-1252 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki, 他4名: "Synthesis of Novel Chiral Oligopyridine Derivative Ligands for the Enantioselectie Addition of Diethylzinc to Benzaldehyde"Tetrahedron : Asymmetry. 9. 3203-3212 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki, 他3名: "A New Convenient Friedel-Crafts Alkylation of Aromatic Compounds with Secondary Alcohol Mothanesulfonates in the Presence of Scandium (III) Trifluoromethanesulfonate or"Synthesis. 603-606 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Gamoh,K.Emi,H.Kotsuki: "Optical Resolution by Immobilized Lipase"Chromatography. 20. 26-27 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki, 他3名: "Sc (OTf) _3-and TfoH-Catalyzed Baeyer-Villiger Oxidation of Carbonyl Compounds with m-Chloroperbenzoic Acid"Synlett. 462-464 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] 小槻日吉三: "キラルトリフラート法-光学活性天然物合成の新手法"有機合成化学協会誌. 57. 334-345 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki, 他3名: "Trifluoromethane Sulfonic Acid, an Unusually Powerful Catalyst for the Michael Addition Reaction of β-Ketoesters under Solvent-Free Conditions"Journal of Organic Chemistry. 64. 3770-3773 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki, 他3名: "Ytherbium (III) Trifluoromethanesulfonate-Catalyzed Homoconjugate Addition of β-Ketoesters with Activated Cyclopropane Derivatives at High Pressure"Synlett. 650-652 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki, 他4名: "A New Enantioselective Total Synthesis of A I-77-B"Organic Letters. 1. 499-502 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki, 他3名: "A New Quinazoline Synthesis"Synlett. 1993-1995 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] 蒲生啓司,坂田知栄子,小槻日吉三: "UDS-ショ糖エステルに固定化したリパーゼの有機溶媒中での酵素活性およびエナンチオ選択性"分析化学. 48. 1149-1155 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki, 他3名: "A New Facile Method for the Synthesis of 4-Dialkylammopyridine Derivatives by High Pressure-Promoted Amination of 4-Chloropyridine"Synlett. 116-118 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki, 他3名: "A Novel Synthesis of a Highly Sterically Hindered CT Symmetric Chiral Pyridine Derivative"Heterocycles. 52. 661-666 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Matsuoka, 他5名: "Immunochemical Analysis of a Photoreceptor Protein Using Anti-IP3 Receptor Antibody in the Unicellular Organism, Blepharisma"Journal of Photochemistry & Photobiology, B. 54. 131-135 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Matsuoka, 他7名: "Analyses of Structure of Photoreceptor Organelle and Blepharismin-associated Protein in Unicellular Eukaryote Blepharisma"Photochemistry & Photobiology. 72. 709-713 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] 蒲生啓司,小槻日吉三: "高圧条件下における血清アルブミンへの分子テンプレート形成に関する研究"分析化学. 49. 551-556 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki, 他3名: "A Novel Synthesis of Chiral DBU/DBN-Related Molecules for Use in Asymmetric Base Catalysis"Heterocycles. 53. 2561-2567 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kojima, 他4名: "A New Practical Method for Regioselective Nucleophilic Aromatic Alkylation of ortho-or para-Methoxy-substituted Aromatic Esters with Grignard Reagents"Tetrahedron Letteres. 42. 1709-1712 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Shinohara, 他2名: "Asymmetric Baeyer-Villiger Oxidation of Cyclobatanones Using Diethlzinc/Oxygen/Chiral Amino Alcohols"Heterocycles. 55. 237-242 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Ohishi, 他4名: "High-yielding Tforl-catalyzed Condensation of Phends with Aromatic Aldehydes at High Pressure. A Model Study of the Blepharismn"Tetrahedron Letters. 42(印刷中). (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Matsuoka,H.Kotsuki: "Photosensory Transduction in Unicellular Eukaryote Blepharisma"Journal of Experimental Zoology. (印刷中). (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] D.Tokumori, 他4名: "In vivo Photosensory Structure in Unicellular Eukaryote Blepharisma"Microbios. (印刷中). (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] A.Kida, 他4名: "Study on Primary Stage in Photosignal Transduction Leading to Step-up Photophobic Response in the Unicellular Eukaryote, Blepharisma"Microbios. (印刷中). (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] 小槻日吉三 他2名: "不斉Baeyer-Villiger酸化の新展開"オレオサイエンス. (印刷中). (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] 林,富岡,米光 編: "Asymmetric Synthesis : Graphical Abstracts and Experimental Methods"講談社. 396 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] 松本澄,井畑敏一 編: "超高圧有機合成-高効率分子変換と反応制御を目指して-"ナカニシヤ出版. 466 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki: "Scandium (III) Trifluoromethanesulfonate-Catalyzed Friedel-Crafts Alkylation of Aromatic Compounds with Secondary Alcohol Methanesulfonates"Synlett. 255-256 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki: "Solvent-Free Organic Reactions on Silica Gel Supports. Facile Transformation of Epoxides to β-Halohydrins with Lithium Halides"Tetrahedron. 54. 2709-2722 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki: "Organic Synthesis at High Pressure. Efficient Ring Opening Reaction of Epoxides with Heterocycles (Invited Review)"Rev.High Pressure Sci.Technol.. 7. 1250-1252 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki: "A Facile New Method for Selective Deprotection of N-(tert-Butoxycarbonyl)-Protected Carboxamides with Yb(OTf)_3 Supported on Silica Gel"Tetrahedron Lett.. 39. 4869-4870 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki: "Synthesis of Novel Chiral Oligopyridine Derivative Ligands for the Enantioselective Addition of Diethylzinc to Benzaldehyde"Tetrahedron : Asymmetry. 9. 3203-3212 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki: "A New Convenient Friedel-Crafts Alkylation of Aromatic Compounds with Secondary Alcohol Methanesulfonates in the Presence of Scandium (III) Trifluoromethanesulfonate or Trifluoromethanesulfonic Acid as the Catalyst"Synthesis. 603-606 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Gamoh: "Optical Resolution by Immobilized Lipase"Chromatography. 26-27 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki: "Sc(OTf)_3-and TfOH-Catalyzed Baeyer-Villiger Oxidation of Carbonyl Compounds with m-Chloroperbenzoic Acid"Synlett. 462-464 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Matsumoto: "Nakanishiya"High Pressure Organic Synthesis. 466 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki: "Chiral Triflate Technology : An Efficient Tool for the Construction of Biologically Interesting Natural Products in Optically Pure Forms"Yuki Gosei Kagaku Kyokai-Shi. 57. 334-345 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki: "Trifluoromethanesulfonic Acid, an Unusually Powerful Catalyst for the Michael Addition Reaction of β-Ketoesters under Solvent-Free Conditions"J.Org.Chem.. 64. 3770-3773 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki: "High-Pressure Organic Chemistry.Part 22. Ytterbium (III) Trifluoromethanesulfonate-Catalyzed Homoconjugate Addition Reactions of β-Ketoesters with Activated Cyclopropane Derivatives at High Pressure"Synlett. 650-652 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki: "A New Enantioselective Total Synthesis of AI-77-B"Organic Lett.. 1. 499-502 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki: "A New Quinazoline Synthesis"Synlett. 1993-1995 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Gamoh: "Catalytic Activity and Enantioselectivity in Organic Solvent of Lipase Immobilized on ODS-sugar Ester"BUNSEKIKAGAKU. 48. 1149-1155 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki: "High-Pressure Organic Chemistry.Part 23. A New Facile Method for the Synthesis of 4-Dialkylaminopyridine Derivatives by High-Pressure-Promoted Amination of 4-Chloropyridine"Synlett. 116-118 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki: "A Novel Synthesis of a Highly Sterically Hindered C_2-Symmetric Chiral Pyridine Derivative"Heterocycles. 52. 661-666 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Matsuoka: "Immunochemical Analysis of a Photoreceptor Protein Using Anti-IP3 Receptor Antibody in the Unicellular Organism, Blepharisma"J.Photochem.Photobiol., B.. 54. 131-135 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Matsuoka: "Analyses of Structure of Photoreceptor Organelle and Blepharismin-associated Protein in Unicellular Eukaryote Blepharisma"Photochem.Photobiol.. 72. 709-713 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Gamoh: "Molecular Template Formation on Serum Albumin under a High-pressure Condition"BUNSEKIKAGAKU. 49. 551-556 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki: "A Novel Synthesis of Chiral DBU/DBN-Related Molecules for Use in Asymmetric Base Catalysis"Heterocycles. 53. 2561-2567 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kojima: "A New Practical Method for Regioselective Nucleophilic Aromatic Alkylation of ortho- or para-Methoxy-substituted Aromatic Esters with Grignard Reagents"Tetrahedron Lett.. 42. 1709-1712 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Shinohara: "Asymmetric Baeyer-Villiger Oxidation of Cyclobutanones Using Diethylzinc/Oxygen/Chiral Amino Alcohols"Heterocycles. 55. 237-242 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Ohishi: "High-yielding TfOH-catalyzed Condensation of Phenols with Aromatic Aldehydes at High Pressure. A Model Study of Blepharismin"Tetrahedron Lett.. (in press)..

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Matsuoka: "Photosensory Transduction in Unicellular Eukaryote Blepharisma"J.Exp. Zool.. (in press)..

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] D.Tokumori: "In vivo Photosensory Structure in Unicellular Eukaryote Blepharisma"Microbios. (in press)..

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] A.Kida: "Study on Primary Stage in Photosignal Transduction Leading to Step-up Photophobic Response in the Unicellular Eukaryote, Blepharisma"Microbios. (in press)..

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Kotsuki: "Recent Developments in Asymmetric Baeyer-Villiger Oxidation"Oleoscience. (in press)..

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Hayashi: "Asymmetric Synthesis : Graphical Abstracts and Experimental Methods"Kodansha. 396 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Matsuoka 他5名: "Immunochemical Analysis of a Photoreceptor Protein Using Anti-IP3 Receptor Antibody in the Unicellular Organism, Blepharisma"Journal of Photochemistry & Photobiology, B.. 54. 131-135 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Matsuoka 他7名: "Analyses of Structure of Photoreceptor Organelle and Blepharisma associated Protein in Unicellular Eukaryote Blepharisma"Photochemistry & Photobiology. 72. 709-713 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] 蒲生啓司,小槻日吉三: "高圧条件下における血清アルブミンへの分子テンプレート形成に関する研究"分析化学. 49. 551-556 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] H.Kotsuki 他3名: "A Novel Synthesis of Chiral DBU/DBN-Related Molecules for Use in Asymmetric Base Catalysis"Heterocycles. 53. 2561-2567 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Kojima 他4名: "A New Practical Method for Regioselective Nucleophilic Aromatic Alkylation of ortho-or para-Methoxy substituted Aromatic・・・・"Tetrahedron Letters. 42. 1709-1712 (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Shinohara 他2名: "Asymmetric baeyer-villiger oxidation of cyclobutanones using diethylzinc / oxygen / chiral amino alcohols"Heterocycles. 55. 237-242 (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Ohishi 他4名: "High-yielding TfOH-catalyzed Condensation of Phenols with Aromatic Aldehydes at High Pressure, A Model Synthesis of the Benzylidene・・・・"Tetrahedron Letters. 42(印刷中). (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Matsuoka,H.Kotsuki: "Photosensory Transduction in Unicellular Eukaryote Blepharisma"Journal of Experimental Zoology. (印刷中). (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] D.Tokumori, 他4名: "In vivo Photosensory Structure in Unicellular Eukaryote Blepharisma"Microbios. (印刷中). (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] A.Kida, 他4名: "Study on Primary Stage in Photosignal Transduction Leading to Stepup Photophobic Response in the Unicellular Eukaryote・・・・"Microbios. (印刷中). (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] 小槻日吉三 他2名: "不斉Baeyer Villiger酸化の新展開"オレオサイエンス. (印刷中). (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] K.Gamoh,K.Emi,H.Kotsuki: "Optical Resolution by Immobilized Lipase"Chromatography. 20. 26-27 (1999)

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  • [Publications] H.Kotsuki,他3名: "A New Convenient Friedel-Crafts Alkylation of Aromatic Compounds with Secondary Alcohol Methanesulfornates in the Presence of Sc(OTf)3 or・・・"Synthesis. 603-606 (1999)

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  • [Publications] H.Kotsuki,他3名: "Sc(OTf)3- and TfOH-Catalyzed Baeyer-Villiger Oxidation of Carbonyl Compounds with m-Chloooperbenzoic Acid"Synlett. 462-464 (1999)

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  • [Publications] 小槻 日吉三: "キラルトリフラート法-光学活性天然物合成の新手法"有機合成化学協会誌. 57. 334-345 (1999)

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  • [Publications] H.Kotsuki,他3名: "Trifluoromethanesulfonic Acid,an Unusually Powerful Catalyst for the Michael Addition Reaction of β-Ketoesters under Solvem-Free Conditions"Journal of Organic Chemistry. 64. 3770-3773 (1999)

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  • [Publications] H.Kotsuki,他3名: "Ytlerbium(III) Trifluoromethanesulfonate-Catalyzed Homoconjugate Addition of β-Ketoesters with Astivated Cyclopropane Derivatives at High Pressure"Synlett. 650-652 (1999)

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  • [Publications] H.Kotsuki,他4名: "A New Enantioselective Total Synthesis of AI-77-B"Organic Letters. 1. 499-502 (1999)

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  • [Publications] H.Kotsuki,他3名: "A New Quirazoline Synthesis"Synlett. 1993-1995 (1999)

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  • [Publications] 蒲生啓司,坂田知栄子,小槻日吉三: "ODS-ショ糖エステルに固定化したリパーゼの有機溶媒中での酵素活性およびエナンチオ選択性"分析化学. 48. 1149-1155 (1999)

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  • [Publications] H.Kotsuki,他3名: "A New Facile Method for the Synthesis of 4-Dialkylaminopyridine Derivatives by High Pressure-Promoted Amination of 4-Chloropyridine"Synlett. 116-118 (2000)

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  • [Publications] H.Kotsuki,他3名: "A Novel Synthesis of a Highly Sterically Hindered G-Symmetric Chiral Pyridine Derivative"Heterocycles. 52. 661-666 (2000)

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  • [Publications] T.Matsukoka,他5名: "Immunochemical Analysis of a Photoreceptor Protein Using Anti-IP3 Receptor Antibody in the Unicellutar Organism,Blepharisma"Journal of Photochemistry & Photobiology. (印刷中). (2000)

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  • [Publications] 松本 澄・井畑敏一.編: "超高圧有機合成-高効率分子変換と反応制御を目指して-"ナカニシヤ書店. 466 (1999)

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  • [Publications] H.Kotsuki: "Solvont-Free Organsc Reactions on Silica Gel Supports Fauile Transformasion of Epoxides to B-halohydrins with Lithium Halides" Tetrahodron. 54. 2709-2722 (1998)

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  • [Publications] H.Kotsuki: "A Facile New Method for Solective Deprolecdion of N-(tert-Butoxycarboyl)-Protected Carboxamides with Yb(OTf)3 Supported on Silica Gel" Tetrahodron Letlers. 39. 4869-4870 (1998)

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  • [Publications] H.Kotsuki: "Scandium(III)Trifluoromethane sulfonate-Catalyzed Friedol-Crofts Alkylation of Aromatic Conpounds with Secondary Alcohol Methanesfulfonates" Synlett. 255-256 (1998)

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  • [Publications] H.Kotsuki: "Organic Synthesis at High Pressure.Efficient Ring Opening Reaction of Epoxides with Heterocyclos" Review of High Pressure Scionce & Technology. 7. 1250-1252 (1998)

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  • [Publications] H.Kotsuki: "Soprthesis of Novel Chiral Oligopyridine Derivartve Ligands for the Enantioselective Addition of Dietlylzinc to Benzaldehyde." Tetrahodron:Asymmetry. 9. 3203-3212 (1998)

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  • [Publications] H.Kotsuki: "A New Conveniont Friedel-Ceafts Alkylarion of Aromatic Cosypoinds with Secondary slcohol Methanesatforates in the Prescnce of Scandium(III)Taifluoronerhanesulfomte or" Sgnthesis. 印刷中. 印刷中 (1999)

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  • [Publications] H.Kotsuki: "Sc(OTf)3-and TfOH-Caralyzed Baeyer-Valliger Oxidation of Carbonyl Compounds with m-Chloroperbenzoic Acid" Synlett. 印刷中. 印刷中 (1999)

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  • [Publications] H.Kotsuki: "Trifheoromerhanesultonic Auid,an Unusually Poqerful Catalyst forthe Michael Addition Roacrion of B-Keroestcrs under Solvent-Free Conditions" Journal of Organic Chemistry. 64 印刷中. 印刷中 (1999)

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  • [Publications] H.Kotsuki: "Ytterbium(III) Trsfluoromerhanesuiforate Catolyced Homocoryusate Additim Rcactions of B-Ketoestcrs with Bctivased Cyclopropane Derivasies at lhigh Pressure" Synlett. 印刷中. 印刷中 (1999)

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      1998 Annual Research Report
  • [Publications] 小槻 日吉三: "キシルトリフラート法-光学活性天然物合成の新手法" 有機合成化学協会誌. 57 印刷中. 印刷中 (1999)

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  • [Publications] 林・富岡・米光 編: "Asymmedric Symrheais:Geaphical Absrocts and Expeaimenal Mefhals" 講談社, 396 (1998)

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  • [Publications] 松本 澄 編: "超高圧有機合成-高効率分子交換と反応制御を目指して-" ナカニミヤ出版 印刷中, 印刷中 (1999)

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      1998 Annual Research Report

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Published: 1998-04-01   Modified: 2016-04-21  

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