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Development and Utilization of Versatile Chirl Building Blocks

Research Project

Project/Area Number 10557205
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section展開研究
Research Field Chemical pharmacy
Research InstitutionTohoku University

Principal Investigator

OGASAWARA Kunio  Tohoku University, Graduate School of Pharmaceutical Sciences, Professor, 大学院・薬学研究科, 教授 (60004602)

Co-Investigator(Kenkyū-buntansha) SUGAHARA Tsutomu  Tohoku University, Graduate School of Pharmaceutical Sciences, Research Instructor, 大学院・薬学研究科, 助手 (50006350)
TANIGUCHI Takahiko  Tohoku University, Graduate School of Pharmaceutical Sciences, Associate Professor, 大学院・薬学研究科, 助教授 (90271915)
HIROYA Kou  Tohoku University, Graduate School of Pharmaceutical Sciences, Associate Professor, 大学院・薬学研究科, 助教授 (70192721)
YOSHIDA Naoyuki  Chisso Corporation, Senior Researcher, 主任研究員
TAKAHASHI Michiyasu  Tohoku University, Graduate School of Pharmaceutical Sciences, Research Associate, 大学院・薬学研究科, 教務職員 (80089789)
Project Period (FY) 1998 – 2001
Project Status Completed (Fiscal Year 2001)
Budget Amount *help
¥12,800,000 (Direct Cost: ¥12,800,000)
Fiscal Year 2001: ¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 2000: ¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1999: ¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1998: ¥7,000,000 (Direct Cost: ¥7,000,000)
Keywordschiral building block / substrate-controlled synthesis / diastereocontrolled synthesis / enantiocontrolled synthesis / natural product synthesis / asymmetric synthesis / enzymatic resolution / kinetic resolution / キラルシクロペンタジエノン / キラルシクロヘキサジエノン / 触媒的分割 / 酵素的分割 / 不斉水素転移反応 / 酵素的分割反応 / コンベックス面選択性 / キラルシクロペンタジエン / キラルシクロヘキサジエン / リパーゼ触媒反応 / 逆ディールス・アルダー反応
Research Abstract

During the present investigation, three versatole chiral building blocks exhibiting convex-face selectivity have been developed by employing either enzymatic or chemical kinetic resolution method. All building blocks possess an enone and a masked enone moieties which allowed diastereocontrolled modification owing to their inherent stereochemical nature. Versatility of these chiral molecules as chiral building blocks were demonstrated by enantio- and diastereocontrolled construction of a variety of physiologically active natural products synthesized in the present investigation are prostaglandins (key intermediate), (-)-morphine, (+)-tanikolide, (-)-malyngolide, (-)-kainic acid, (+)-febrifugine, (+)- and (-)-levoglucosenone, (-)-shikimic acid, (-)-semburine, (-)-antirhine, (-)-quinine (key intermediate), (+)-uleine, (-)-aristeromycin, (+)-arnicenone, (-)-physostigmine, (-)-physovenine, (-)-aphanorphine, (-)-iridolactone, (+)-pedicularis-lactone, simplactone A, (-)-tetrahydrolipstatin, eight aldohexoses, six conduritols, pseudomonic acids, ferruginol, (+)-20R-dihydrocleavamine, (-)-quebrachamine, (-)-menisdaurilide, (-)-mesembrine, and (+)-sceletinum A.

Report

(5 results)
  • 2001 Annual Research Report   Final Research Report Summary
  • 2000 Annual Research Report
  • 1999 Annual Research Report
  • 1998 Annual Research Report
  • Research Products

    (36 results)

All Other

All Publications (36 results)

  • [Publications] Keigo Tanaka 他2名: "7,7-Dimethyl-6,8-dioxabicyclo[3,3,0]oct-3-en-2-one as a synthetic equivavalentof ketodi-cyclopentadiene : a new to(-)-physostigmine,(-)-physovenine, and (-)-aphanorphine"tetrahedron Lett.. 42・6. 1049-1052 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Yosuke Iura 他2名: "Enantion-and Diastereocontrolled Synthesis of an Angular Triquinane Sesquiterpene (+)-Arnicenone"Org. Lett.. 3・2. 291-293 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Hideyuki Tanaka 他5名: "Enantion-and diastereocontrolled synthesis of (-)-iridolactone and (+)-pedicularis-lactone"Org. Lett.. 3・5. 679-681 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Masayuki Sato 他6名: "A new chiral route to 5-and 6-substituted hydrophran-2-ones utilizing enantiopure 4-cumyloxy-2-cyclopenten-1-one"Tetrahedron Lett.. 42・15. 2833-2837 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Masatoshi Honzumi 他2名: "A New Convergent Route to Aldohexoses from a Common Chiral Building Block"Org. Lett.. 3・9. 1355-1358 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Takahiko Taniguchi 他1名: "A diastereocontrolled route to the tetrahydropyran nucleus of pseudomonic acids"Tetrahedron Lett.. 42・19. 3359-3361 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Yosuke Iura, Tsutomu Sugahara, Kunio Ogasawara: "Enantio- and Diastereocontrolled Synthesis of an Angular Triquinane Sesquiterpene (+) -Arnicenone"Org. Lett.. 3. 291-293 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Keigo Tanaka, Takahiko Taniguchi, Kunio Ogasawara: "7,7-Dimethyl-6,8-dioxabicyclo [3,3.0] oct-3-en-2-one as a synthetic equivalent ketodicyclojpentadiene: a new route to (-)-physostigmine, (-) -physovenine, and (-)-aphanorphine"Tetrahedron Lett.. 42. 1049-1052 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Hideyuki Tanaka, Takashi Kamikubo , Naoyuki Yosida, Hideki Sakagami, Takahiko Taniguchi, Kunio Ogasawara: "Enantio- and Diastereocontrolled Synthesis of (-)-Iridolactone and (+) -Pedicularis-lactone"Org. Lett.. 3. 679-681 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Masayuki Sato, Hiromi Nakashima, Keisuke Hanada, Masato Hayashi, Masatoshi Honzumi, Takahiko Taniguchi and Kunio 0gasawara: "A new chiral route to 5- and 6-substituted hydropyran-2-ones utilizing enantiopure 4-cumyloxy-2-cyclopenten-1-one"Tetrahedron Lett.. 42. 2833-2837 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Masatoshi Honzumi, Takahiko Taniguchi, and Kunio Ogasawara: "A New Convergent Route to Aldohexoses from a Common Chiral Building Block"Org. Lett.. 3. 1355-1358 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Takahiko Taniguchi and Kunio Ogasawara: "A diastereocontrolled route to the tetrahydropyran nucleus of pseudomonic acids"Tetrahedron Lett.. 42. 3359-3361 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Keigo Tanaka他2名: "7,7-Dimethyl-6, 8-dioxabicyclo[3.3.0]oct-3-en-2-one as a synthetic equivavalentof ketodicyclopentadiene : a new route to(-)-physostigmine, (-)-physovenine, and(-)-aphanorphine"Tetrahedron Lett.. 42・6. 1049-1051 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Yosuke Iura他2名: "Enantio-and Diastereocontrolled Synthesis of an Angular Triquinane Sesquiterpene(+)-Arnicenone"Org.Lett.. 3・2. 291-293 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Hideyuki Tanaka他5名: "Enantio-and diastereocontrolled synthesis of(-)-iridolactone and (+)-pedicularis-lactone"Orb.Lett.. 3・5. 679-681 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Masayuki Sato他6名: "A new chiral route to 5-and 6-substituted hydropyran-2-ones utilizing enantiopure 4-cumyloxy-2-cyclopenten-1-kne"Tetrahedron Lett. 42・15. 2833-2837 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Masatoshi Honzumi他2名: "A New Convergent Route to Aldohexoses from a Common Chiral Building Block"Oeg.Lett.. 3・9. 1355-1358 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Rika Muto他1名: "Annulation of a 3-methoxycyclopentenone onto a cyclopentenol double bond by intramolecular Pauson-Khand reaction"Tetrahedron Lett. 42・25. 4143-4146 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Regina Mikie Kaanada 他2名: "Asymmetric hydrogen transfer protocol for a synthesis of (+)-frontalin and (-)-malyngolide"Tetrahedron Lett.. 41. 3631-3635 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Keigo Tanaka 他4名: "A Concise Route to (+)-Estron"Org.Lett.. 2. 1915-1917 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Regina Mikie Kaanada 他2名: "The First Synthesis of (+)-Tanikolide, a Toxic and Antifungal Lactone from the Marine Cyanobactetrium Lyngbya majuscula"Synlett. 1019-1021 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Adel S,ElAzab 他2名: "An Expedient Route to the Calabar Bean Alkaloids (-)-Physovenine and (-)-Physostigmin"Org.Lett.. 2. 2757-2759 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Hirosi Nakagawa 他2名: "A Concise Route to (-)-Kainic acid"Org.Lett.. 2. 3181-3183 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Hiroshi Nagata 他2名: "Diasterodivergent Synthesisof the C9-Cyclopentanone Chiral building Block"Synthesis. 521-524 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Hiromi Nakashima 他3名: "Lipase-mediated Reaction of cis-4-Cumyloxy-2-cyclopenten-1-ol and Its Utilization for Enantioconvergent Preparation of (-)-Oxabicyclo[3.3.0] oct-6-in-3-one"Synlett. 1754-1756 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Masatoshi Honzumi 他2名: "Integrated synthesis of conduritol A〜F using a single chiral building block"Chem.Commun.. 1985-1986 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Naoyuki Yoshida 他4名: "Preparation of a synthetic equivalent of chiral menthyl 2,5-dihydroxycyclohexane-1,4-dicarboxylate"Tetrahedron : Asymmetry. 10. 3849-3857 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Hiromi Nakashima 他3名: "A Stereocontrolled Route to (-)-Epibatidine Using a Chiral cis-Cyclohexadiene-1,4-diol Equivalent"Synlett. 1405-1406 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Takahiko Taniguchi 他4名: "Lipase-mediated Preparation of Sugar Building Blocks"Synthesis. 1325-1330 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Miwako Takeuchi 他2名: "Back to the Sugars: A New Enatio and Diastereocontrolled Route to Hexoses from Furfural"Synthesis. 341-354 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Takashi Kamikubo: "Absolute Configuration of(+)-PT-Toxin:Enantiodivergent Synthesis of (+)-And(-)-PT-Toxins" Heterocycles. 47. 69-72 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Takashi Kamikubo: "First Enantiocontrolled Synthesis of Sceletium alkaloid A-4:Determination of the absolute configuration" Chem.Commun.783-784 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Naoyuki Yoshida: "A Concise Synthesis of(-)-Neplanocin A" Tetrahedron Lett.39. 4677-4678 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Regina Mikie Kanada: "Asymmetric Hydrogen Transfer Protocol for Enantiocontrolled Synthesis of (-)-Chokol G" Chem.Commun.1755-1756 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Kou Hiroya: "A concise enantio-and diastereo-controlled synthesis of(-)-quinic acid and (-)-shikimic acid" Chem.Commun.2033-2034 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Osamu Yamada: "Asymmetric Synthesis of Sceletium Alkaloids:(-)-Mesembrine,(+)-Sceletium A-4,(+)-Tortuosamine and (+)-N-Formyltortuosamine" Tetrahedron Lett.,. 39. 7747-7750 (1998)

    • Related Report
      1998 Annual Research Report

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

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