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Asymmetric Total Synthesis of Chiral Molecules

Research Project

Project/Area Number 05234102
Research Category

Grant-in-Aid for Scientific Research on Priority Areas

Allocation TypeSingle-year Grants
Research InstitutionOkayama University of Science (1994-1995)
Hokkaido University (1993)

Principal Investigator

YONEMITSU Osamu  Okayama University of Science, Faculty of Science, Professor, 理学部, 教授 (60001038)

Co-Investigator(Kenkyū-buntansha) YAMADA Kiyoyuki  Nagoya University, Graduate School of Science, Professor, 大学院・理学研究科, 教授 (90022540)
MORI Kenji  Science University of Tokyo, Faculty of Science, Professor, 理学部, 教授 (20011843)
HASHIMOTO Shun-ichi  Hokkaido University, Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (80107391)
TAKAHASHI Takashi  Tokyo Institute of Technology, Faculty of Engineering, Professor, 工学部, 教授 (80110724)
HIRAMA Masahiro  Tohoku University, Graduate School of Science, Professor, 大学院・理学研究科, 教授 (30165203)
池上 四郎  帝京大学, 薬学部, 教授 (10119555)
Project Period (FY) 1993 – 1995
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥100,100,000 (Direct Cost: ¥100,100,000)
Fiscal Year 1995: ¥40,200,000 (Direct Cost: ¥40,200,000)
Fiscal Year 1994: ¥31,100,000 (Direct Cost: ¥31,100,000)
Fiscal Year 1993: ¥28,800,000 (Direct Cost: ¥28,800,000)
Keywordsasymmetric total synthesis / organic natural product / optically active chiral compound / selective reaction / biologically active compound / multi-step synthesis / condensation reaction / protecting group
Research Abstract

Asymmetric synthesis of complex chiral compounds such as useful natural products is one of important purposes of modern synthetic chemistry. This project "asymmetric total synthesis of chiral molecules" was carried out by about 20 synthetic chemists for three years beginning in 1993. Target molecules of this project, divided in four groups, are not only structurally complex compounds with many chiral centers and functional groups but also quite useful compounds with important biological activities and new functions : 1) Regulatory compounds of biological functions. 2) Chemical signal compounds. 3) Pharmacologically and physiologically active compounds. 4) Biologically active natural products produced in ultramicroquantity. During three years, we obtained many noteworthy results such as new synthetic methods of prostacyclines and prostaglandins, asymmetric synthesis and absolute configuration determination of various pheromons, computer-aided synthesis of enediyn compounds, hapten synthesis of ciguatoxin, synthesis of the crucial intermediate of taxol, asymmetric synthesis of tetracyclins, total synthesis of antitumor aplyronine A,lactone-ring synthesis of tedanolide, and total synthesis of hygrolidin.

Report

(4 results)
  • 1996 Final Research Report Summary
  • 1995 Annual Research Report
  • 1994 Annual Research Report
  • 1993 Annual Research Report
  • Research Products

    (30 results)

All Other

All Publications (30 results)

  • [Publications] O.Yonemitsu: "Radical Cyclization Using a Thioacetal Group for Radical Generation." Tetrahedron. 52. 9713-9734 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] O.Yonemitsu: "Total Synthesis of 16-Membered Tetraene Macrolide Hygrolidin." Tetrahedron Lett.37. 9077-9080 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Hirama: "Synthesis of Epoxy Enediyne Core Intermediates Related to Neocarzinostatin." Tetrahedron Lett.37. 9335-9338 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S.Hashimoto: "Stereocontrolled Synthesis of the C1-C17 and C18-C25 Subunits of Hygrolidin." Tetrahedron Lett.37. 9073-9076 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Takahashi: "Synthesis of 10-Membered Masked Oxaenediyne Analogue of Kedacridin." Tetrahedron Lett.37. 2433-2436 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Mori: "A New Synthesis of Faranal,the Trail Pheromone of the Pharaoh's Ant." Liebigs Annalen. 12. 2089-2092 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] O.Yonemitsu: "Radical Cyclization Using a Thioacetal Group for Radical Generation." Tetrahedron. 52. 9713-9734 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] O.Yonemitsu: "Total Synthesis of 16-Membered Tetraene Macrolide Hygrolidin." Tetrahedron Lett.37. 9077-9080 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Hirama: "Synthesis of Epoxy Enediyne Core Intermediates Related to Neocarzinostatin." Tetrahedron Lett.37. 9335-9338 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S.Hashimoto: "Stereocontrolled Synthesis of the C1-C17 and C18-C25 Subunits of Hygrolidin." Tetrahedron Lett.37. 9073-9076 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Takahashi: "Synthesis of 10-Membered Masked Oxaenediyne Analogue of Kedacridin." Tetrahedron Lett.37. 2433-2436 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Mori: "A New Synthesis of Faranal, the Trail Pheromone of the Pharaoh's Ant." Liebigs Annalen. 12. 2089-2092 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] O. Yonemitsu: "Stereoselective Total Synthesis of Lysocellin, the Representative Polyether Antibiotic of the Lysocellin Family. Part 2." Tetrahedron. 52. 551-564 (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] O. Yonemitsu: "Synthetic Studies of 18-Membered Anti-Tumor Macrolide, Tedanolide." Tetrahedron Lett.37. 385-388 (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] M. Hirama: "Enantio-Controlled Synthesis of the AB Ring Moiety of Ciguatoxin." Synlett. 1252-1254 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] S. Hashimoto: "Asymmetric Cretion of Quaternary Carbon Centers by Enantiotopically Selective Aromatic C-H Insertion Catalyzed by Chiral Dirhodium (II) Carboxylates." Tetrahedron Letters. 36. 1491-1494 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] K. Mori: "A New Synthesis of Faranall [( 3S, 4R, 6E, 10Z) -3, 4, 7, 11-Tetramethyl-6, 10-tridecadienal], the Trail Pheromone of the Pharaoh's Ant, Monomoriun pharaonis" Liebige Annalen. 12. 2089-2092 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] K. Yamada: "Total Synthesis of Aplyronine A, a Potent Antitumor Subatance of Marine Origin." J. Am. Chem. Soc.116. 7443-7444 (1994)

    • Related Report
      1995 Annual Research Report
  • [Publications] O.Yonemitsu: "Lewis Acid-Prompted Diastereoselective Radical Cyclization Using Chiral α,β-Unsaturated Esters." J.Am.Chem.Soc.116. 6455-6456 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] S.Ikegami: "Enantioselective Intramolecular C-H Insertions of α-Diazo β-Keto Esters Catalyzed by Dirhodi(II) Tetrakis〔N-phthaloyl-(S)-phenylalanine〕." SYNLETT. 353 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] T.Takahashi: "Synthesis of An Elicitor-Active Hexaglucoside Analogue by One-Pot, Two-Step Glycosidation Procedure." J.Am.Chem.Soc.116. 7919 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] S.Hashimoto: "Enhancement of Enantioselectivity in Intramolecular C-H Insertion Reactions of α-Diazo β-Keto Esters Catalyzed by Chiral Dirhodium(II) Carboxylates." Tetrahedron Lett.34. 5109 (1993)

    • Related Report
      1994 Annual Research Report
  • [Publications] K.Mori: "Pheromone Synthesis, CLXIII. Synthesis of (9Z,25S,26R,43Z)-25,26-Epoxy-9,43-henpenta-contadiene and Its Antipode." Liebigs Ann. Chem.695 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] K.Yamada: "Absolute Stereochemistry of Aplyronine A, a Potent Antitumor Substance of Marine Origin." J.Am.Chem.Soc.116. 7441 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Horita, K.: "Stereoselective Total Synthesis of Polyether Ionophore Antibiotics, Isolasalocid A and Lasalocid A. Part 1. Highly Stereocontrolled Construction of the C-Rings (C_<18>-C_<24>) by Acid-Catalyzed Cyclization of Methoxyphenylallyl Alcohols." Tetrahedron. 49. 5979-5996 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Horita, K.: "Stereoselective Total Synthesis of Polyether Ionophore Antibiotics, Isolasalocid A and Lasalocid A. Part 2. The Total Synthesis via Stereoselective Construction of the B-Rings by Chelation-Controlled Cyclization under Thermodynamic Conditions." Tetrahedron. 49. 5997-6018 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Hashimoto, S.: "Enhancement of Enantioselectivity in Intramolecular C-H Insertion Reactions of α-Diazo β-Keto Esters Catalyzed by Chiral Dirhodium(II)Carboxylates." Tetrahedron Lett.34. 5109-5112 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Horita, K.: "Synthetic Studies of Halichondrin B, a Antitumor Polyether Macrolide Isolated from a Marine Sponge. 2. Efficient Synthesis of C16-C26 Fragments via Construction of the D Ring by a Highlty Stereocontrolled Iodoetherification." Synlett. 40-43 (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] Horita, K.: "Synthetic Studies of Halichondrin B, a Antitumor Polyether Macrolide Isolated from a Marine Sponge. 3. Synthesis of the C27-C36 Subunit via Completely Stereoselective C-Glycosylation to the F Ring." Synlett. 43-45 (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] Horita, K.: "Synthetic Studies of Halichondrin B, a Antitumor Polyether Macrolide Isolated from a Marine Sponge. 4. Synthesis of the C37-C54 Subunit via Stereoselective Construction of Three Consecutive J,K,and L Rings." Synlett. 46-48 (1994)

    • Related Report
      1993 Annual Research Report

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Published: 1993-04-01   Modified: 2021-12-07  

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