• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to project page

1995 Fiscal Year Final Research Report Summary

Synthetic Studies for Ample Supply of Biologically Active Natural Products

Research Project

Project/Area Number 05303011
Research Category

Grant-in-Aid for Co-operative Research (A)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionNgasaki University

Principal Investigator

IRIE Hiroshi  Ngasaki University, Department of Pharmacuetical Sciences, Profesor, 薬学部, 教授 (00025686)

Co-Investigator(Kenkyū-buntansha) YOSHIMOTO Tadashi  Nagasaki University, department of Pharmacuetical Sciences, Profesor, 薬学部, 教授 (60088870)
TOMIOKA Kiyoshi  Osaka University Institute of Scientific and Industrial Research, Professor, 産業科学研究所, 教授 (50114575)
FUJII Nobutaka  Kyoto University Department of Pharmacutical Sciences, Professor, 薬学部, 教授 (60109014)
SHIBASAKI Masakatsu  University of Tokyo, Department of Pharmacutical Sciences, Professor, 薬学部, 教授 (30112767)
HASHIMOTO Syunichi  Hokkaido University, Department of Pharmacutical Sciences, Professor, 薬学部, 教授 (80107391)
Project Period (FY) 1993 – 1995
KeywordsBiologically active natural products / Asymmetric Synthesis / Organometalic Chenistry / Modification of amino acid / Development of chiral synthon / Ample supply of useful enzymes
Research Abstract

Reacenty, many biologically active natural products, which are available to the precise investigation of the biological transmission mechanism in molecular level, have been isolated and characterized. However, it is quite dificult to obtain such kind of compounds from natural sources. For example, it is well-known that some spider toxins inhibit the exitement neuro-transmimmision in brain and are suitable tool to investigate such transmission mechanism. Since the gain of these toxins in pure forms from natural sources is impossible, their ample supplies have been required by their syntheses. Irie and his co-workers (Nagasaki University and Hokkaido University) have accomplished a new method to synthesize these toxins using the azide group in the place of amino group for the construction of the polyamine side chains in toxins. This method makes the supply of the considerably large amount of toxins possible. Tkahashi (Tokyo Institute of Technology) has developed a new method which is available to synthesize some biologically active poly-succaride chains. Fujii (Kyoto University) has synthesized some poly-peptides having an possibility to develop of new drug against AIDS.Uemura (Shizuoka Unversity) investigated the toxic substances produced by a marine shell and elucidated the structure of genuin toxin possessing the possibility to design new drug. And all the members of this project have carried out high-lebel of research works evluated all the world and published large number of the reports on international scientific journals.

  • Research Products

    (52 results)

All Other

All Publications (52 results)

  • [Publications] M.Miyashita: "Total Synthesis of Nephilatoxin-8(NPTX-^*),a New Neurotoxin of Joro Spider(Nephila clavata)" Chemistry Letters. 929-932 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Miyashita: "Enantioselective Synthesis of (-)-Serricornin,a Sex Pheromone of a Female Cigarette Beetle(LasiodermaserricomeF.)" Tetrahedron Asymmetry. 4. 1573-1578 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Hatakeyama: "Enantiospecific Synthesis of (+)-Paeonilactone C and (+)-Paeoniflorigenone from R-(-)-Carvone" Tetrahedron Lett.35. 7993-7996 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Hatakeyama: "An Efficient Route to a Key A-Ring Synthon for 1,25-Dihydroxyvitamin D3 and its Analogs" Tetrahedron. 50. 13369-13376 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Hatakeyama: "Total Synthesis of (+)-Paeonilactone B and (-)-Paeonisuffrone" Tetrahedron Lett,. 36. 267-268 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Miyashita: "Total Synthesis of Nephilatoxin-7(NPTX-7),a New Neurotoxin of Joro Spider(Nephila clavata)" Tetrahedron Lett. 36. 5231-5234 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Miyashita: "An Efficient Synthesis of JSTX-3,a Potent Neurotoxin of Joro Spider(Nephila clavata)" Tetrahedron. 51. 10687-10698 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Hashimoto: "Double Asymmetric Inductiom in Intramolecular C-H Insertion Reaction of α-Diazo β-Keto Esters" Synthetic Communications. 24. 3277-3287 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] N.Watanabe: "Asymmetric Creation of Quaternary Carbon Centers by Enantiotopically Selective Aromatic C-H Insertion Catalyzed by Chiral Dirhodium (II)Carboxylates" Tetrahedron Lett.36. 1491-1494 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Hashimoto: "A New Access to Mori's Intermediate for the Paractical Synthesis of (-)-Periplanone-B" Chemistry Lett,. 1091-1092 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Tokuda: "Synthesis of Hybrid Molecule Containing Neocarzinostatin Chromophore Analogue and Minor Groove Binder" Tetrahedron Letters.34. 669-672 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Takahashi: "Synthesis and Binding of Simple Neocarzinostatin Chromophore Analogues to the Apoprotain" Tetrahedron,Symposia in Print,. 50. 1327-1340 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] J.Maruyama: "Synthesis of(±)-Pinoresinol and its Related Compound using Potassium Persulfate(K_2S_2O_8)Oxidation of Benzoylacetate" Heterocycles. 37. 839-845 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Kuroda: "Studies on the Structure-Toxicity Relationship of AK-Toxin,a Host-Specific Toxin to Japanese White Pear,Produced by Altermaria kukuchiana:Synthesis of Methyl(2S,5R)-4-(N-Acetylphenylalanyl)oxy-5,6-epoxy-5-methylhex-2(E)-enoate and its Steroisomers" Chem.Pharm.Bull.35. 1328-1339 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Hatakeyama: "Enantiospecific Synthesis of (+)-Paeonilactone C and (+)-Paeoniflorigenone from R-(-)-Carvone" Tetrahedron Lett,. 35. 7993-7996 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Hatakeyama: "An Efficient Route to a Key A-Ring Synthon for 1,25-Dihydrtoxyvitamin D3 and its Analogs" Tetrahedron,. 50. 13369-13376 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Hatakeyama: "Total Synthesis of (+)-Paeonilactone B and (-)-Paeonisuffrone" Tetrahedron Lett,. 36. 267-268 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Hatakeyama: "An Enantioselective Synthesis of(11R,12S,13S,9Z,15ZO-9,12,13-Trihydroxyoctadeca-9,15-dienoic Acid,A Self-defensive Substance against Rice Blast Disease" Chemistry Lett,. 763-764 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Yamaguchi: "Chemistry and Antimicrobial Activity of Caryoynencins Analogus" J.Med.Chem.38. 5015-5022 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Takano: "Concise Enantiodivergent Synthesis of Eutypoxide" J.Chem.Soc.,Chem.Commun.614-615 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Samizu: "An Expedient Route to Indole-3-acetic Acid Derivatives" Synlett. 499-500 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Shin: "A New Synthesis of the Naturally Occurring Free Radical Scavenger Carazostatin" Chem.Lett.289-290 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Hiroi: "Palladium-catalyzed Intermolecular Asymmetric Metallo-Ene Reactions via Allylic Sulfinate-Sulfone Rearrangement" Chem.Pharm.Bull.42. 1036- (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Sasai: "The First Heterobimetallic Multifunctional Asymmetric Catalyst" J.Am.Chem.Soc.117. 6194-6198 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Saito: "Total Synthesis of (±)-Furaquinocin D" J.Am.Chem.Soc.117. 10757-10758 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Takahashi: "Synthesis of Dynemicin A Analogue and Its Bergman-Type Cycloaromatization" Angew.Chem.Int.Ed.Engl.34. 1345-1348 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] D.Uemura: "Pinnatoxin A:A Toxic Amphoteric Macrocycle from Okinawa Bivalva Pinna muriata" J.Am.Chem.Soc.117. 1155-1156 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] N.Sugimoto: "Mobility Inhibition and Nematocidal Activity of Asarone and Related Phenylpropanoids on Second-Stage Larvae of Toxocare canis" Biol.Pharm.Bull.18. 605-609 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Fuji: "An Enantioselective Synthesis of (-)-Psudophrynaminol though Asymmetric Nitroolefination" Synlett,. 367- (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Tamamura: "Synthesis of Protegrin-Related Peptides and Their Antibacterial and Anti-Human Immunodeficiency Virus Activity" Chem.Pharm.Bull.43. 853-858 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Kanai: "Asymmetric Conjugate Addition of Organomagnesium Cuprates Controlled by Stoichiometric Amount of Chiral Phosphine" Tetrahedron Lett,. 36. 4273-4274 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Kan: "Internal Activation of Acrylate-type Dienophiles in Diels-Alder Reactions" Tetrahedron Lett.,. 36. 943-946 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Hatakeyama: "A Facile Stereoselective Route to a C/D-Ring Synthon for 20-Epi-2-oxavitamine D3 Analogues" J.Chem.Soc.,Chem.Commun.1959-1960 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Sagara: "Specific Affinity Labeling of m Opioid Recepters in Rat Brain by S-Activated Sulfidyldihydromorphine Analogues" Bioorg.Med.Chem.Lett,. 5. 1609-1614 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Fujita: "6-O-Sulfonates of Cycloinulohexaose(Cyclofructan-6)" Tetrahedron Lett.35. 2197-2200 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Suga: "Prolidase from Xanthomonas maltophilia:Purification and Characterization of the Enzyme" Biosci.Biotech.Biochem.59. 2087-2090 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Miyashita, M.Matsushita, H.Sato, T.Toki, T.Nakajima, and H.Irie: "Total Synthesis of Nephilatoxin-8 (NPTX-8), a New Neurotoxin of Joro Spider (Nephila clavata)" Chemistry Letters. 929-932 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] J.Koyama, T.Ogura, K.Tagahara, and H.Irie: "Synthesis of 5,6,7,8-Tetrahydroquinolines by Thermo-lysis of Oxime O-Allyl Ethers in the Presence of Boron Trifluoride Etherate" Chem.Pharm.Bull.41. 1297-1298 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Fujimoto, H.Miyagawa, T.Tsurushima, H.Irie, K.Okamura, and T.Ueno: "Structures of Antafumicine A and B,Novel Antifungal Substances Produced by the Fungus Aspergillus nigar NH-401" Biosci.Biotech.Biochem.57. 1222-1224 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Miyashita, Y.Toshimitsu, T.Shiratani, and H.Irie: "Enantioselective Synthesis of (-) -Serricornin, a Sex Pheromone of a Female Cigarette Beetle (Lasioderma serricorne F.)" Tetrahedron Asymmetry. 4. 1573-1578 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Miyashita, K.Yoshihara, K.Kawamine, M.Hoshino, and H.Irie: "Synthetic Studies on Polypropionate Antibiotics Based on the Stereospecific Methylation of gamma, delta-Epoxy Acrylates by Trimethylaluminum. A Highly Stereoselective Const-ruction of the Eight Contiguous Chiral Centers of Ansa-chains of Rifamycins" Tetrahedron Letters. 34. 6285-6288 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] D.Tanaka, T.Yoshino, I.Kouno, M.Miyashita, and H.Irie: "Synthesis of Monoterpene Lactones, (+) -Boschnia-lactone and (+) -Isoiridomyrmecin, Starting from L- (+) -Arabinose" Tetrahedron. 49. 10253-10262 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] J.Maruyama, M.Kobayashi, M.Miyashita, I.Kouno, and H.Irie: "Synthesis of (<plus-minus>) -Pinoresinol and its Related Compound using Potassium Persulfate (K_2S_2O_8) Oxidation of Benzoylacetates" Heterocycles. 37. 839-845 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Kuroda, M.Miyashita, H.Irie, and T.Ueno: "Studies on the Structure-Toxicity Relationship of AK-Toxin, a Host-Specific Toxin to Japanese White Pear, Produced by Alternaria kikuchiana : .Synthesis of Methyl (4S,5R) - 4- (N-Acetylphenylalanyl) oxy-5,6-epoxy-5-methylhex-2 (E) -enoate and its Stereoisomers" Chem.Pharm.Bull.42. 1328-1330 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S.Htakeyama, M.Kawamura, S.Takano, and H.Irie: "Enantiospecific Synthesis of (+) -Paeonilactone C and (+) -Paeoniflorigenone from R- (-) -Carvone" Tetrahedron Letters. 35. 7993-7996 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S.Hatakeyama, H.Irie, T.Shintani, Y.Noguchi, H.Yamada, and H.Nishizawa: "An Efficient Route to a Key A-Ring Synthon for 1,25-Dihydroxyvitamin D_3 and its Analogs" Tetrahedron. 50. 13369-13376 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S.Hatakeyama, M.Kawamura, Y.Mukugi, and H.Irie: "Total Synthesis of (+) -Paeonilactone B and (-) -Paeonisuffrone" Tetrahedron Letters. 36. 267-268 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S.Hatakeyama, K.Kojima, H.Fukuyama, and H.Irie: "An Enatioselective Synthesis of (11R,12S,13S,9Z,15Z) -9,12,13-Trihydroxyoctadeca-9,15-dienoic Acid, a Self-defensive Substance against Rice Blast Disease" Chemistry Letters. 763-764 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Matsushita, T.Kanemura, S.Hatakeyama, H.Irie, T.Toki, and M.Miyashita: "Total Synthesis of Nephilatoxin-7 (NPTX-7), a New Neurotoxin of Joro Spider (Nephila clavata)" Tetrahedron Letters. 36. 5231-5234 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Matsushita, T.Kanemura, S.Hatakeyama, H.Irie, T.Toki, and M.Miyashita: "An Efficient Synthesis of JSTX-3, a potent Neurotoxin of Joro Spider (Nephila clavata)" Tetrahedron. 51. 10687-10698 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T.Tsurushima, T.Ueno, H.Fukami, H.Irie, and M.Inoue: "Germination Self-Inhibitors from Colltotrichum gloeosporioides f.sp.jussiaea" Molecul.Plant-Microbe Interction. 8. 652-657 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S.Hatakeyama, t.Ikeda, H.Irie, C.Izumi, H.Mori, K.Uenoyama, H.Yamada, and M.Nishizawa: "A Facile Stereoselective Route to a C/D-Ring Synthon for 20-Epi-22-oxavitamin D_3 Analogues" J.Chem.Soc.Chem.Commun. 1959-1960 (1995)

    • Description
      「研究成果報告書概要(欧文)」より

URL: 

Published: 1997-03-04  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi