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Systematic Synthesis of Bioactive Compounds Using Photochemical Method

Research Project

Project/Area Number 12650846
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionTokyo University of Agriculture and Technology

Principal Investigator

CHIBA Kazuhiro  Tokyo University of Agriculture and Technology Dept. of Applied Biological Science, Associate Professor, 農学部, 助教授 (20227325)

Co-Investigator(Kenkyū-buntansha) KITANO Yoshikazu  Tokyo University of Agriculture and Technology Dept. of Applied Biological Science, Assistant Professor, 農学部, 助手 (10302910)
Project Period (FY) 2000 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥3,700,000 (Direct Cost: ¥3,700,000)
Fiscal Year 2002: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 2001: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 2000: ¥2,200,000 (Direct Cost: ¥2,200,000)
KeywordsCombinatorial chemistry / Solid-phase synthesis / Thermomorphic solvent / Photo-induced reaction / electrosynthesis / peptide / 合成ライブラリー / ベンジルスルフィド / 液相合成 / 二相溶液 / 熱特性 / キノンメチド / 固相反応
Research Abstract

Euglobal and robustadials were isolated from Encalyptus spp. as inhibitors of the Epstein-Barr virus activation, or as antimalarial compounds. Previously we reported an electrochemical generation of o-quinomethane and their cycloaddition with α-phellandrene to yield the euglobal Ia_1 and Ia_2 skeletons. Furthermore, the first, concise synthesis of natural euglobals has been accomplished by biomimetic cycloaddition of monotermpenes and quinomethanes generated in situ by oxidation of grandinol. In this paper, we introduced novel thermomorphic reaction systems that enable high-throughput synthesis of eublobal and robustadial skeletons via intermolecular hetero Diels-Alder reaction of terpenes and anodically generatefd o-quinomethanes.the thermomorphic liquid-liquid separation system composed of organic solvents of different polarity might allow for extremely efficient reactions, for example, by the association of apolar products and polar substrates or catalysts in a one-phase solution, w … More hich could be spatially separated after the completion of reactions. It should further open the door for the construction of liquid-phase combinatorial chemistry, industrial and green chemistry by the ease of the separation of products, catalyses, reagents, electrolytes, and/or soluble platforms for organic synthesis. This gave us the incentive to explore a novel thermomorphic reaction system using typical organis solvents. Among numerous compositions of organic solvents, an appropriate mixture of cyclohexane (CH) and nitroalkane (NA) was initially found to show the desired function, that is, a 75 : 25 (v/v) mixture of CH and NA [a 20 : 80 v/v mixture of nitromethane (NM) and nitroethane (NE)]. At 25℃, the solvent mixture was separated into an upper CH(main) phase and a lower NA(main) phase. temperature with an increase in the CH ratio to complete the one-phase formation. By using this system, several euglobal and robustadial skeletons could be synthesized just by changing alkenes (dienophiles for intermolecular hetero-Diels-Alder reaction), and most of the products were isolated from upper layer just by cooling to form the biphasic solution system after the completion of the reaction. Less

Report

(4 results)
  • 2002 Annual Research Report   Final Research Report Summary
  • 2001 Annual Research Report
  • 2000 Annual Research Report
  • Research Products

    (30 results)

All Other

All Publications (30 results)

  • [Publications] Kim, S., Hayashi, K., Kitano, Y., Tada, M., Chiba, K.: "Anodic Modification of Proline Derivatives using a Lithium Perchlorate / Nitromethane Electrolyte Solution"Org.Lett.. 4(21). 3735-3737 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Chiba, K., Kono, Y., Kim, S., Nishimoto, K., Kitano, Y., Tada, M.: "A Liquid-phase peptide synthesis in cyclohexane-based biphasic thermomorphic systems"Chem.Commun.. 1766-1767 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] 山本修, 小澤剛, 笹本忠, 千葉一裕: "アルゴン中におけるC60の熱分解"炭素. 205. 263-265 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Yukiko Mizutani, Yasuki Matsumura, Shinya Matsumoto, Kenji Matsui, Kazuhiro Chiba, Tomohiko Mori: "Factors affecting reaction of cucumber root lipoxygenase in phospholipid vesicle dispersions"Colloids and Surfaces B : Biointerfaces. 25. 171-181 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Chiba, K., Miura, T., Kim, S., Kitano, Y., Tada, M.: "Electrocatalytic Intermolecular Olefin Cross-Coupling by Anodically Induced Formal [2+2] Cycloaddition between Enol Ethers and Alkenes"J.Am.Chem.Soc. 123. 11314-11315 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Ed.By M.S.Workentin, F.Maran, K.Chiba: "Organic Electrochemistry, The Fifth International Manuel M.Baizer Symposium in Honor of Jean Michel Saveant"Electrochemical Society. 162 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Kim, S.; Hayashi, K.; Kitano, Y.; Tada, M.;, Chiba, K.: "Anodic Modification of Proline Derivatives using a Lithium Perchlorate/ Nitromethane Electrolyte Solution"Org. Lett.. 4(21). 3735-3737 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Chaiba; K., Kono. Y.; Kim. S.; Nishimoto. K.; Kitano, Y.; Tada. M. A: "Liquid-phase peptide synthesis in cyclohexane-based biphasic thermomorphic systems"Chem. Commun.. 1766-1767 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Yukiko Mizutani, Yasuki Matsumura, Shinya Matsumoto, Kenji Matsui, Kazuhiro Chiba and Tomohiko Mori: "Factors affecting reaction of cucumber root lipoxygenase in phospholipid vesicle dispersions"Colloids and Surfaces B : Biointerfaces. 25. 171-181 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Chiba. K., Miura. T., Kim. S., Kitano. Y., and Tada. M.: "Electrocatalytic Intermolecular Olefin Cross-Coupling by Anodically Induced Formal[2+2] Cycloaddition between Enol Ethers and Alkenes"J. Am. Chem. Soc.. 123. 11314-11315 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Reddy, S. H. K., Chiba, K., Sun, Y., and Moeller, K. D.: "Anodic oxidations of electron-rich olefins : radical cation based approaches to the synthesis of bridged bicyclic ring skeletons"Tetrahedron. 57(24). 5183-5197 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Kitano, Y.; Chiba, K.; Tada, M.: "Highly Efficient Conversion of Alcohols to Isocyanides"Synthesis. 3. 437-443 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Chiba, K.; Uchiyama, R.; Kim, S.; Kitano, Y.; Tada, M.: "Benzylic Intermolecular Carbon-Carbon Bond Formation by Selective Anodic Oxidation of Dithioacetals"Org. Lett.. 3(8). 1245-1248 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Kim, S., Kitano, Y., Tada, M., and Chiba, K.: "Benzylic Natroalkylayion by Paired Electrolysis of Benzyl Sulfides in Nitroalkanes"J. Electroanal. Chem.. 507(1-2). 152-156 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Chiba, K.; Kono, Y.; Kitayama, M.; Uchiyama, R.; Kim, S.; Kitano, Y.; Toda, M.: "A Perfluorinated Micellar Reaction System In Lithium Perchllorate/Acetonitrile ; Enhanced Efficiency in Anodic Electron-Transfer and Intermolecular Cycloassition"Electrochemistry Communications.. 3(2). 63-66 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Yukiko Mizutani, Yasuki Matsumura, Shinya Matsumoto, Kenji Matsui, Kazuhiro Chiba, Tomohiko Mori: "Factors affecting reaction of cucumber root lipoxygenase in phospholipid vesicle dispersions"Colloids and Surfaces B : Biointerfaces. 25. 171-181 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Kim, S., Hayashi, K., Kitano, Y., Tada, M., Chiba, K.: "Anodic Modification of Proline Derivatives using a Lithium Perchlorate /Nitromethane Electrolyte Solution"Org.Lett.. 4(21). 3735-3737 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Chiba, K., Kono, Y., Kim, S., Nishimoto, K., Kitano, Y., Tada, M.: "A Liquid-phase peptide synthesis in cyclohexane-based biphasic thermomorphic systems"Chem.Commun.. 1766-1767 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] 千葉一裕: "熱特性を利用した有機溶媒液/液二相系による反応-分離法"日本農薬学会誌. (印刷中). (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.S.Workentin, F.Maran, K.Chiba: "Organic Electrochemistry"The Electrochemical Society. 162 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] K.Chiba 他: "Electrocatalytic Intermolecular Olefin Cross, Coupling"J.Am.Chem.Soc.. 123. 11314-11315 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Reddy, K.Chiba 他: "Anodic Oxidations of Electron-Rich Olefins"Tetrahedron. 57. 5183-5197 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Y.Kitano, K.Chiba 他: "Highly Efficient Conversion of Alcohols to Isocyanides"Synthesis. 3. 437-443 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] S.Kim, K.Chiba 他: "Benzylic Nitroalkylation by Paired Electrolysis"J.Electroanal.Chem. 507. 152-156 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Chiba: "Benzylic Intermolecular Carbon-Carbon Bond Formation by selective Anodic Oxidation"Org.lett.. (印刷中). (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] S.Kim: "Benzylic Nitroalkylation by paired Electrolysis of Benzyl Sulfides in Nitroclkanes"J.Electroanal.chem. (印刷中). (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] K.Chiba: "A Perfluorinated Micellar Reaction System In Lithium Porchlorate/Acetonitrile"Electrochemistry Communications. 3(2). 63-66 (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] Z.Yang: "Synthesis of Varigusly Oxidized Abietane Diterpenes and Their Antibacterial Activities Against NRSA and VRE"Bioorg.Med.Chem. 9(2). 347-356 (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] M.Tada: "Synthesis of (+) and (-)-femginal via osymmetric cyclization of a pdyene"J.Chem.Soc,Perkin Trans 1. 2657-2664 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] S.Kim: "Alkylindan Synthesis via an Intermolecular [3+2] cycloaddition Between Unactivated Alkenes and in situgenerated p-Quinomethanes "Tetrahedron Lett. 41. 7079-7083 (2000)

    • Related Report
      2000 Annual Research Report

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Published: 2000-04-01   Modified: 2016-04-21  

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