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Exploitation of Chiral Epichlorohydrin as Versatile Chiral Building Block

Research Project

Project/Area Number 07557288
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section展開研究
Research Field Chemical pharmacy
Research InstitutionTOHOKU UNIVERSITY

Principal Investigator

OGASAWARA Kunio  Tohoku University Faculty of Pharmaceutical Sciences Professor, 薬学部, 教授 (60004602)

Co-Investigator(Kenkyū-buntansha) TAKAHASHI Michiyasu  Tohoku University Faculty of Pharmaceutical Sciences Assistant, 薬学部, 教務職員 (80089789)
SUGAHARA Tsutomu  Tohoku University Faculty of Pharmaceutical Sciences Assistant Professor, 薬学部, 助手 (50006350)
HIROYA Kou  Tohoku University Faculty of Pharmaceutical Sciences Associated Professor, 薬学部, 助教授 (70192721)
Project Period (FY) 1995 – 1997
Project Status Completed (Fiscal Year 1997)
Budget Amount *help
¥6,500,000 (Direct Cost: ¥6,500,000)
Fiscal Year 1997: ¥2,800,000 (Direct Cost: ¥2,800,000)
Fiscal Year 1996: ¥3,700,000 (Direct Cost: ¥3,700,000)
Keywordsepichlorohydrin / chiral building block / enantiocontrolled synthesis / muscarine / O-benzylglycidol / fish deterrent / vitamin D / HMG-CoA reductase / コレステロール生合成阻害剤 / HMG Co-A還元酵素阻害 / compactin / mevinolin / カルシウム代謝ホルモン / calcitriol / 活性型ビタミンD / 生体抗酸化物質 / carbazoquinocin A / carbazoquinocin D / sporochnol A / 魚摂食阻害物質 / キラルエピクロロヒドリン / キラルグリシドール / カルシトリオール / コリンエステラーゼ阻害剤
Research Abstract

Epichlorohydrin was obtained practically in enantiomerically pure forms by fermentation in our country. In order to exploit enantiomerically pure epichlorohydrin as versatile chiral building block, we have investigated enantiocontrolled construction of a variety of physiologically active natural products including amino acids, alkaloids, polyketides, terpenes, and steroids. During a 1995-1997 period, we have been engaged in the enantiocontrolled syntheses of "Sporochnol A", the fish deterrent from the Caribbean Marine alge, "carbazoquinocins A and D", the potent lipid peroxidation inhibitors from Streptomyces violaceus 2248-SVT2, "compactin lactone", the essential structural component associated with the biological activity of the potent HMG-CoA reductase compactin, "calcitriol enyne", the a ring component of the activated form of vitamin D,"dihydroxyheliotridane", a physiologically interesting necine base, and "muscarine and three naturally occurring its diastereomers", mushroom poisons exhibiting potent anticholinergic activity. Among these compounds obtained, the absolute configurations of sporochnol A,carbazoquinocins A and D were determined by these syntheses by correlation to the absolute configuration of epichlorohydrin used as the starting material.

Report

(4 results)
  • 1997 Annual Research Report   Final Research Report Summary
  • 1996 Annual Research Report
  • 1995 Annual Research Report
  • Research Products

    (28 results)

All Other

All Publications (28 results)

  • [Publications] Keigo, Tanaka: "An Expedient Route to Optically Pure 3-end-Hydroxycyclopentadiene" Synthesis. 1237-1239 (19985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takashi, Kamikubo: "The Enantiodivergent Total Synthesis of Natural and Unnatural Enantiomers of Theobroxide" Tetrahedron Lett.36. 1685-1688 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takashi, Kamikubo: "Concise Enantiocontrolled Synthesis of the A-ring Precursor of Calcitriol from Chiral Cyclohexakiene Synthon" J.Chem.Soc.,Chem.Commun.1951-1952 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kou, Hiroya: "Asymmetrization of meso 1,4-Enediol Ethers by Chiral BINAP-Rh(I)Catalyzed Isomerization" Angew.Chem.Int.Ed.Engl.34. 2287-2289 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kou Hiroya: "Catalytic Asymmetrization of meso-3,7-Bis-siloxycycloheptene by Chial Rhodium(I)-binap[2,2'-bis(diphenylphosphino)-1,1'binaphthyl]Catalyst:the Enantiocontrolled Asymmetric Synthesis of(-)-(S)-Physoperuving" J.Chem.Soc.,Chem.Commun.2205-2206 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Tutomu, Suhahara: "Contro-Sterric Diels-Alder Route to 3-Oxodicyclopentadiene and Meso 3,5-endo-Dihydroxy-4,5-dihydrodicyclopentadiene" Tetrahidron Lett.37. 205-208 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kogyoku, Shin: "Enantiotopical Synthesis of carbazoquinocins A and D,the Potent Lipid Peroxidation Inhibitors from Streptomyces violaceus 2448-SVT2" Synlett. 922-924 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Michiyasu, Takahashi: "The Absolute Configuration of(+)-Sporochnol A,the Fish Deterrent from the Caribbean Marine Alga Sporchus bolleanus" Tetrahedron:Asymmetry. 8. 1235-1242 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Mitsuru, Oizumi: "A Unified Procedure for Diastereo-and Enaatiocontrolled Construction of Compactin Lactone and calcitriol Enyne" Synlett. 1111-1113 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Keigo Tanaka: "An Expedient Route to Optically Pure 3-end-Hydroxycyclopentadiene" Synthesis. 1237-1239 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takashi Kamikubo: "The Enantiodivergent Total Synthesis of Natural and Unnatural Enantiomers of Theobroxide" Tetrahedron Lett.36. 1685-1688 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takashi Kamikubo: "Concise Enantiocontrolled Synthesis of the A-ring Precursor of Calcitriol from Chiral Cyclohexadiene Synthon" J.Chem.Soc., Chem.Commun.1951-1952 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kou Hiroya: "Asymmetrization of meso 1,4-Enediol Ethers by Chiral BINAP-Rh (I) Catalyzed Isomerization" Angew.Chem.Int.Ed.Engl.34. 2287-2289 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kou Hiroya: "Catalytic Asymmetrization of meso-3,7-Bis-siloxycycloheptene by Chial Rhodium (I) -binap [2,2'-bis (diphenylphosphino) 1,1'binaphthy1] Catalyst : the Enantiocontrolled Asymmetric Synthesis of (-) - (S) -Physoperuvine" J.Chem.Soc., Chem.Commun.2205-2206 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Tutomu Sugahara: "Contra-Sterric Diels-Alder Route to 3-Oxo-dicyclopentadiene and Meso 3,5-endo-Dihydroxy-4,5-dihydrodicyclopentadiene" Tetrahedron Lett.37. 205-208 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kogyoku Shin: "Enantiotopical Synthesis of Carbazoquinocins A and D,the Potent Lipid Peroxidation Inhibitors from Streptomyces violaceus 2448-SVT2" Synlett. 922-924 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Michiyasu Takahashi: "The Absolute Configuration of (+) -Sporochnol A,the Fish Deterrent from the Caribbean Marine Alga Sporochus bolleanus" Tetrahedron : Asymmetry. 8. 1235-1242 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Mitsuru Oizumi: "A Unified Procedure for Diastereo-and Enantiocontrolled Construction of Compactin Lactone and Calcitriol Enyne" Synlett. 1111-1113 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Michiyasu Takahashi: "The Absolute Configuration of (+)-Sporochnol A,the Fish Deterrentfrom the Caribbean Marine Alga Sporochus bolleanus" Tetrahedron:Asymmetry. 8・8. 1235-1242 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Mitsuru Oizumi: "A Unified Procedure for Diastereo-and Enantiocontrolled Construction of Compactin Lactone and Calcitriol Enyne" Synlett. ・9. 1111-1113 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Kogyoku Shin: "Enantiotopical Synthesis of Carbazoquinocins A and D, The Potent Lipid Peroxidation Inhibitors from Streptomyces violaceus 2448-SVT2" Synlett. 922-924 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Michiyasu Takahashi: "The Absolute Configuration of (+) -Sporochnol A, the Fish Deterrent from the Caribbean Marine Alga Sporohnus bolleanus" Tetrahedron : Asymmetry. (発表予定). (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] K. Tanaka: "An Expedient Route to Optically Pure 3-endo-Hydroxycyclopentadiene" Sythesis. 1237-1239 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] T.Kamikubo: "The Enantiodivergent Total Synthesis of Natural and Unnatural Enantiomers of Theobroxide" Tetrahedron Lett.36. 1685-1688 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] T. Kamikubo: "Concise Enantiocontrolled Synthesis of the A-Ring Precursor of Calcitriol from the Chiral Cyclohexadienone Synthon" J. Chem. Soc., Chem. Commun.1951-1952 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] K.Hiroya: "Asymmetrization of meso 1,4-Enediol Ethers by Chiral BINAP-RH(I)Catalyzad Isomerization" Angew. Chem. Int. Ed. Engl.34. 2287-2289 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] K. Hiroya: "Catalytic Asymmetrization of meso-3, 7-Bis-siloxycycloheptene by Chiaral Rhodium(I)-binap[2, 2′-bis(diphenylphosphino)-1,1′-binaphthyl]Catalyst: the Enantiocontrolled Asymmetric Synthesis of (-)-(S)-Physoperuvine" J. Chem. Soc., Chem. Commun.2205-2206 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] T. Sugahara: "Contra-Steric Diels-Alder Route to 3-Oxodicyclopentadiene and Meso 3,5-endo-Dihydroxy-4, 5-dihydrodicyclopentadiene" Tetrahedron Lett.37. 205-208 (1996)

    • Related Report
      1995 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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