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2001 Fiscal Year Final Research Report Summary

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
Keywordschiral building block / substrate-controlled synthesis / diastereocontrolled synthesis / enantiocontrolled synthesis / natural product synthesis / asymmetric synthesis / enzymatic resolution / kinetic resolution
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.

  • Research Products

    (12 results)

All Other

All Publications (12 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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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

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Published: 2003-09-17  

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