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1990 Fiscal Year Final Research Report Summary

Studies on Biosynthetic Mechanisms of Biologically Active Subsatnces and Their Applications

Research Project

Project/Area Number 63303003
Research Category

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

Allocation TypeSingle-year Grants
Research Field 天然物有機化学
Research InstitutionHokkaido University

Principal Investigator

MURAI Akio  Hokkaido Univ., Fac. Sci., Professor, 理学部, 教授 (20000838)

Co-Investigator(Kenkyū-buntansha) SHIZURI Yoshikazu  Tokushima Bunri Univ., Sci. Pharm. Professor, 薬学部, 教授 (90135294)
SUGA Takayuki  Hiroshima Univ., Fac. Sci., Professor, 理学部, 教授 (00033811)
SANKAWA Ushio  Tokyo Univ., Fac. Pharm., Professor, 薬学部, 教授 (60012613)
OGURA Kyozo  Tohoku Univ., Chem. Res. Inst. Non-Aq. Soln., Professor, 非水溶液化学研究所, 教授 (80006303)
SHIRAHAMA Haruhisa  Hokkaido Univ., Fac. Sci., Professor, 理学部, 教授 (00000802)
Project Period (FY) 1988 – 1990
KeywordsGlycinoeclepin A / Biosynthesis / Biogenetic Pathway / Biorhythm / Active Substance / Polyprenol / Palytoxin / Intramolecular Stacking
Research Abstract

1. Synthesis of a C/D ring system analogue of glycinoeclepin A, a hatching substance for soybean cyst nematode and confirmation of its hatching activity (Murai). 2. Ring formation of the mother skeletons of two biologiccally active terpenes, grayanotoxin and vinigrol, by the radical reactions with Sml2 (Shirahama). 3. Isolation of the protein factor activating solanesyl diphosphate from some fungus and clarification of its mechanism for activation (Ogura). 4. Isolation, structure determination, and total syntheses of two chemical substances controlling the biorhythm of opening and shutting of the soybean leaves (Shizuri). 5. Isolation and structure determination of new polyprenols from soybeans and clarification of the hydrogen elimination mechanism in their Z-prenyl chain extention processes (Suga). 6. Isolation and reaction of palytoxin carboxylic acid as a plausible biosynthetic precursor of palytoxin (Uemura). 7. Structure elucidation of the flower pigments, lobelinin A, B, and ternatin derivatives, and clarification of an intramolecular stacking structure as their general stabilization mechanisms (Goto and Kondo). 8. Clarification of the biosynthetic pathways of the diterpenes isolated from the brown algae (Kakisawa) and the sulfur-containing phytoalexins isolated from Brassica oleracea (Takasugi). Clarification of fatty acid synthase and the reaction mechanism of an antibiotic, cerulenin (Kawaguchi). Isolation of a new frog alkaloid (Tokuyama). Syntheses of the precursors available for the biosynthetic studies (Kakinuma, Tokoroyama, Katsuki, Maki, Hirama, Nozoe, Niwa, Fuji, and Ito). Studies on the enzyme catalyzing the conversion of flavanone into the Isoflavone skeleton (Sankawa).

  • Research Products

    (80 results)

All Other

All Publications (80 results)

  • [Publications] F.Matsuda and H.Shirahama: "Chemistry of ThreeーDimensional Polycyclic Molecules" E.Osawa and O.Yonemitsu,

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] R.E.Grell,E.Lewitzki,and D.Uemura: "The Na,KーPump Part B: Cellular Aspects" A.B.Maunsbach and I.G.Norby, 393---400 (1988)

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      「研究成果報告書概要(和文)」より
  • [Publications] Y.Hirata,D.Uemura,Y.Ohizumi: "Handbook of Natural Toxins Vol.3" A.T.Tu, 241---258 (1988)

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      「研究成果報告書概要(和文)」より
  • [Publications] D.Uemura and Y.Hirata: "Studies in Natural Products Chemistry,Vol.5B" AttaーurーRahman, 377---401 (1989)

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      「研究成果報告書概要(和文)」より
  • [Publications] D.Uemura: "Bioorganic Marine Chemistry" P.J.Scheuer, 1---31 (1991)

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      「研究成果報告書概要(和文)」より
  • [Publications] K. Hayano, H. Shirahama, and T. Matsumoto: "A Cyclopropane Sliding Reaction of *^3-African-10-yl Cation" Bull. Chem. Soc. Jpn.63. 628-629 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] M. Hashimoto, T. Kan, K. Nozaki, M. Yanagiya, H. Shirahama, and T. Matsumoto: "Total Synthesis of(+)-Thyrsifefol, (+)- Thyrsiferol 23-Acetate, and(+)-Venustatriol" J. Org. Chem.55. 5088-5107 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] M. Hashimoto, H. Harigaya, M. Yanagiya, and H. Shirahama: "Total Synthesis of the meso-Triterpene Polyether Teurilene" J. Org. Chem.

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      「研究成果報告書概要(欧文)」より
  • [Publications] K. Monde, N. Katsui, A. shirata, and M. Takasugi: "Brassicanals A and B, Novel Sulfur-Containing Phytoalexins from the Chinese Cabbage Brassica campestris L. ssp. pekinensis" Chemistry Lett.209-210 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] K. Monde, K, sasaki, A. Shirata, and M. Takasugi: "4-Methoxybrassinin, a Sulful-Containing Phytoalexin from Brassica oleracea" Phytochemistry. 29. 1499-1500 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] K. Monde, M. Takasugi, J. A. Lewis, and G. R. Fenwick: "Time-Course Studies of Phytoalexins and Glucosinolates in UV-lrradiated Turnip Tissue" Z. Naturforsch., C.

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      「研究成果報告書概要(欧文)」より
  • [Publications] K. Monde, K. Sasaki, A. shirata, and M. Takasugi: "Brassicanal C and Two Dioxindoles from Brassica oleracea var. capitata" Phytochemistry.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K. Monde and M. Takasugi: "Biosynthesis of cruciferous Phytoalexins : Involvement of a Molecular Rearrangement in the Biosynthesis of Brassinin" J. Chem. Soc., Chem. Commun.

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      「研究成果報告書概要(欧文)」より
  • [Publications] K. Monde, K. sasaki, A. Shirata, and M. Takasugi: "Methoxybrassinins A and B, Two Sulfur-Containing Stress Metabolites from Brassica oleracea" Phytochemistry.

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      「研究成果報告書概要(欧文)」より
  • [Publications] T. Suzuki, O. sato, and M. Hirama: "Two Diverse Modes of Aromatization of a New 10-Membered Ring Analogue of Neocarzinostatin Chromophore" Tetrahedron Lett.31. 4329-4332 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] T. Suzuki, O. Sato, and M. Hirama: "Palladium Catalyzed Stereospecific Cyclization of Hydroxy Epoxides. Stereocontrolled Synthesis of Cis-and Trans-2-alkenyl-3-hydroxytetrahydropyrans" Tetrahedron Lett.31. 4747-4750 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] T. Tanaka, K. Fujiwara, and M. Hirama: "Oxidative Triggering for Aromatization of the Neocarzinostatin Chromophore" Tetrahedron Lett.31. 5947-5950 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] M. Ishiguro, S. Imajo, and M. Hirama: "Modeling Study of the Structure of Macromolecular Antitumor Antibiotics, Neocarzinostatin. The Origin of the Stabilization of the Chromophore" J. Med. Chem.

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      「研究成果報告書概要(欧文)」より
  • [Publications] M. Hirama, T. Noda, S. Yasuda, and S. lto: "Simple Strategy for the Synthesis of the Avermectin-Milbemycin Family. Total Synthesis of Milbemycin alpha1" J. Am. Chem. soc.

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      「研究成果報告書概要(欧文)」より
  • [Publications] K. Fujiwara, H. Sakai, and M. Hirama: "Enyn[3]cumulene. Synthesis and Mode of Aromatization" J. Org. Chem.

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      「研究成果報告書概要(欧文)」より
  • [Publications] T. oishi, M. Hirama, L. R. Sita, and S. Masamune: "Synthesis of Chiral 2, 2'-Bipyrrolidine Derivatives" Synthesis.

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      「研究成果報告書概要(欧文)」より
  • [Publications] M. Kitaoka, H. Nagaki, T. Kinoshita, M. Kuribayashi, T. Koyama, and K. Ogura: "Negative Ion Fast Atom Bombardment-Tandem Mass Spectrometry for Structural Analysis of Isoprenoid Diphosphates" Anal. Biochem.185. 182-186 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] K. Koyama, H. lnoue, S. Ohnuma, and K. Ogura: "Prenyltransferase Reaction Involving Enantiomeric Discrimination--- Enzymatic Synthesis of(S)-10, 11-Epoxyfarnesol from Racemic 6, 7-Epoxyfarnesol Diphosphate and Isopentenyl Diphosphate" Tetrahedron Lett.31. 4189-4190 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] S. Ohnuma, T. Koyama, and K. Ogura: "Enzymatic Synthesis of Glycinoprenols" Tetrahedron Lett.32. 241-242 (1991)

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      「研究成果報告書概要(欧文)」より
  • [Publications] H. Sagami, S. Matsuoka, and K. Ogura: "Formation of Z, E, E-Geranylgeranyl Diphosphate by Rat Liver Microsomes" J. Biol. Chem.

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      「研究成果報告書概要(欧文)」より
  • [Publications] S. Matsuoka, H. Sagami, A. kurisaki, and K. Ogura: "Variable Product Specificity of Microsomal Dehydrodolichyl Diphosphate Synthase from Rat Liver" J. Biol. Chem.

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      「研究成果報告書概要(欧文)」より
  • [Publications] T. Ohta, A. Hosoi, T. kimura, N. Sato, K. Izawa, and S. Nozoe: "Chirospecific Synthesis of Amino Acids and Analogues" Amino Acids. 10-20 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] T. Ohta, S. Shiokawa, R. Sakamoto, and S. Nozoe: "Diastereospecific Synthesis of (-)-Statine" Tetrahedron Lett.31. 7329-7332 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] T. Ohta, S. Shiokawa, E. Iwashita, N. Sato, and S. Nozoe: "Synthesis of(2S, 3S)-3-Hydroxypyroglutamate and Its Application to Carbapenem Synthesis" J. Org. Chem.

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      「研究成果報告書概要(欧文)」より
  • [Publications] I. Shimada, Y. Maki, and H. Sugiyama: "N-Acylation of Stimulant Amino Acids Changes Chiral Recognition of the Flesh Fly Labellar Sugar Site" J. Compt. Physiol.A, 165. 193-196 (1989)

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      「研究成果報告書概要(欧文)」より
  • [Publications] M. O. Ishitsuka, T. Kusumi, A. Ichikawa, and H. Kakisawa: "Bicyclic Diterpenes from Two Species of Brown Algae of the Dictyotaceae" Phytochemistry. 29. 2605-2610 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] S. Seo, A. Uomori, Y. Yoshimura, H. Seto, Y. Ebizuka, H. Noguchi, U. Sankawa, and K. Takeda: "Biosynthesis of Isofucosterol from [2-^<13>C^2H_3]Acetate and[1, 2-^<13>C_2]Acetate in Tissue Cultures of Physalis peruviana-The Stereochemistry of the Hydride Shift from c-24 to C-25" J. Chem. Soc., Perkin Trans I. 105-109 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] U. Sankawa, H. Noguchi, T. Hashimoto, and Y. Yamada: "Non-stereospecific Incorporation of[1, 2-^<13>C_2]Acetate into Tropane Alkaloids in Hyscyamus albus" Chem. Pharm. Bull. 38. 2066-2068 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] T. Hakamatsuka, H. Noguchi, Y. Ebizuka, and U. Sankawa: "Isoflavone Synthase from Cell Suspension Cultures of Pueralia Iobata" Chem. Pharm. Bull.38. 1942-1945 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] M. F. Hashimu, T. Hakamatsuka, Y. Ebizuka, and U. Sankawa: "Reaction Mechanism of Oxidative rearrangement of Flavone in Isoflavone Biosynthesis" FEBS Letters. 271. 219-222 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] K. Ichinose, M. Sugimori, A. Itai, Y. Ebizuka, and U. Sankawa: "Stable Keto-tautomerism of Tetrahydroxynaphthalene in Alkali : Theoretical Support to the Post-Aromatic Reduction in the Biosynthesis of Aromatic Polyketides" Tetrahedron Lett.31. 5905-5908 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] H. Funabashi, A. Kawaguchi, H. Tomoda, S. Omura, S. Okuda, and S. Iwasaki: "Binding Site of Cerulenin in Fatty Acid Synthetase" J. Biochem.105. 751-755 (1989)

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      「研究成果報告書概要(欧文)」より
  • [Publications] N. Yamaguchi and K. Kakinuma: "Biochemical Studies on 2-Deoxy-scyllo-inosose Formation in the 2-Deoxystreptamine Biosynthesis. 1. Facile Chemical Preparation of 2-Deoxy-scyllo-inosose" J. Antibiot.

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      「研究成果報告書概要(欧文)」より
  • [Publications] N. Yamauchi, Y. Fujimoto, and K. Kakinuma: "Biochemical Studies on 2-Deoxy-scylloーinosose Formation in the 2-Deoxystreptamine Biosynthesis. 2. Quantitative Analysis of 2-Deoxy-scyllo-inosose" J. Antibiot.

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      「研究成果報告書概要(欧文)」より
  • [Publications] N. Yamauchi, K. Kakinuma, K. Shimotono, and T. endo: "Biochemical Studies on 2-Deoxy-scyllo-inosose Formation in the 2-Deoxystreptamine Biosynthesis. 3. In Vitro Synthesis of 2-Deoxy-scyllo-inosose with the Cell-Free Extract of Streptomyces Fradie" J. Antibiot.

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      「研究成果報告書概要(欧文)」より
  • [Publications] S. NishiwakiH. Fujiki, M. Suganuma, H. Furuya-Suguri, Y. Iida, M. Ojika, K. Yamada, D. Uemura, F. J. Schmitz, and T. Sugimura: "Estimation of Tumor Promoting Activity and Structure-Function Relationship of Okadaic Acid Derivatives" Carcinogenesis. 11. 1837-1841 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] S. M. Ward, F. Vogalis, D. P. Blondfield, H. Ozaki, N. Fusetani, D, Uemura, N. G. Publicover, and K. M. Sanders: "Inhibition of Electrical Slow Waves and Calcium Currents of Gastric and Colonic Smooth Muscles by Phosphatase Inhibitors" Am. J. Physiol.

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  • [Publications] D. Uemura, T. Chiba, Y. Hayashi, and J. Aiso: "Cytotoxic Alkaloids from the Marine Sponges" J. Nat. Prod.

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      「研究成果報告書概要(欧文)」より
  • [Publications] A. Carl, D. Uemura, N. Fusetani, and K. M. Sanders: "Modulation of Ca^<2+>-Activated K^+Channels by Protein Kinase A and Phosphatase Inhibitors" Am. j. Physiol.

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      「研究成果報告書概要(欧文)」より
  • [Publications] T. Kondo, K. Oki, K. Yoshida, and T. Goto: "Structure of Violdelphin, an Anthocyanin from Violet Flower of Delphinium Hydridum" Chemistry lett.137-138 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] K. Yoshida, T. Kondo, K. Kameda, and T. Goto: "Structure of Anthocyanins Isolated from Purple Leaves of Perilla ocimoides L. Var. crispa Benth and Their Isomerization by Irradiation of Light" Agric. Biol. Chem.54. 1745-1751 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] T. Hoshino and T. Goto: "Effects of pH and Concentration on the Self-Association of Malvin Quinonoidal Base---Electronic and Circular Dichroic Studies." Tetrahedron Lett.31. 1593-1596 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] T. Kondo, M. Ueda, and T. Goto: "Structure of Ternatin B1, A Pentacylated Anthocyanin Substituted on the B-Ring Asymmetrically with Two Long Chains" Tetrahedron. 46. 4749-4756 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] T. Goto and T. Kondo: "Struktur und Molekulare Stapelung von Anthocyanen---Variation der Blufenfarben" Angew. Chem. 10. 17-33 (1991)

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      「研究成果報告書概要(欧文)」より
  • [Publications] T. Goto and T. Kondo: "Structure and Molecular Stacking of Anthocyanins---Flower Color Variation" Angew. Chem. Int. Ed. Eng.30. 17-33 (1991)

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      「研究成果報告書概要(欧文)」より
  • [Publications] H. Niwa, T. Ogawa, and K. Yamada: "Stereoselective Synthesis of(-)-Trachelanthic Acid and (+)-Viridiforic Acid, Necic Acids Components of Pyrrolizidine Alkaloids from a Common Intermediate" Bull. Chem. Soc. Jpn.63. 3707-3709 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] H. Niwa, T. Ogawa, and K. Yamada: "Alkylation of Nucleosides by Dehydromonocrotaline, the Putative Toxic Metabolite of the Carcinogenic Pyrrolizidine Alkaloid Monocrotaline" Tetrahedron Lett.

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      「研究成果報告書概要(欧文)」より
  • [Publications] M. Node, H. Nagasawa, and K. Fuji: "Chiral Total Synthesis of Indole Alkaloids of the Aspidosperma and Hunteria Types" J. Org. Chem.55. 517-521 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] T. Tokoroyama, Y. Kotsuki, H. Matsuyama, T. Shimura, K. Yokotani, and Y. Fukuyama: "Synthetic Studies on Terpenoid Compounds. Part 27. Total Synthesis of Calodendrolide" J. Chem. Soc., Perkin Trans. 1. 1745-1752 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] T. Tokuyama, T. Tsujita, H. M. Garaffo, T. F. Spande, and and J. W. Daly: "Alkaloids from Dendrobatid Poison Frogs : Further Pumillotoxins and Allopumiliotoxins and a Reassignment of the Keto Function in Pumiliotoxin 307F" Tetrahedron.

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      「研究成果報告書概要(欧文)」より
  • [Publications] T. Tokuyama, T. Tsujita, A. Shimada, H. M. Garaffo, T. F. Spande, and J. W. Daly: "Alkaloids from Dendrobatid Poison Frogs : Further cis-Decahydroquinolines and 8-Methylindolizines" Tetrahedron.

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      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yoshioka, R. -Y. Zheng, S. Ohta, and T. Suga: "An Anomaly in the Biosynthesis of(E, E)-Farnesol by the Crude Enzyme System of Pisum Sativum" Phytochemistry. 29. 3467-3472 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Hiraga, S. Izumi, T. Hirata, and T. Suga: "Facile Synthesis of Regioselective Deuteriated(3R)-(-)-[8, 8, 8]-^2H_3]Linalool" Chemistry Lett.49-52 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] T. Suga and T. Endo: "Geranyl Diphosphate Synthase in Leaves of Pelagronium roseum" Phytochemistry.

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      「研究成果報告書概要(欧文)」より
  • [Publications] S. Izumi, M. Aihara, Y. hiraga, T. Hirata, and T. Suga: "Synthesis of[10, 10, 10-^2H_3]Geranyl Diphosphate S. Izumi, D. I. Ito, T. Hirata, and T. Suga, The Facilitation of the Diphosphate Group Elimination feom Geranyl Diphosphate by Chelation of Magnesium lon in the Cyclic Monoterpenoid Biosynthesis" J. Labeled Compd. Radiopharm Tetrahedron Lett.

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      「研究成果報告書概要(欧文)」より
  • [Publications] T. Tsunoda, O. Sasaki, and S. Ito: "AzaーClaisen Rearrangement of Amide Enolates. Stereoselective Synthesis of 2, 3-Disubstituted Carboxamides" Tetrahedron Lett.31. 727-730 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] T. Tsunoda. O. Sasaki, and S. Ito: "An Effective Method for Hydrolysis of N-Monosubstituted Amides via Acetoxy-pivalimides" Tetrahedron Lett.31. 731-734 (1990)

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      「研究成果報告書概要(欧文)」より
  • [Publications] S. Ito and T. Tsunoda: "A Few New Methods for Asymmetric Synthesis" Pure & Appl. Chem.62. 1405-1408 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] R. B. Woodward, W. A. Ayer, J. M. Beaton, F. Bickelhaupt, R. Bonnett, P. Buchchacher, G. L. Closs, H. Dutler, J. Hannah, F. P. Hauck, S. Ito, A. Langemann, E. L. Goff, W. Leimgruber, W. Lwowski, J. Sauer, Z. Valenta, and H. Volz: "The Total Synthesis of Chlorophyll a" Tetrahedron. 46. 7599-7659 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Nishizawa, H. Yamada, J. Sano, S. Ito, Y. Hayashi, H. Ikeda, C. M. Shiro, and H. Tokuda: "Structure of Syzygiol : A Skin-Tumor Promotion Inhibitor" Tetrahedron Lett.32. 211-212 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Hirama, T. Noda, S. Yasuda, and S. Ito: "Simple Strategy for the Synthesis of the Avermectin-Milbemycin Family. Total Synthesis of Milbemycin alpha1" J. Am. Chem. Soc.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Tsunoda, K. Fujiwara, Y. Yamamoto, and S. Ito: "Site-Specific Generation of Nonstabilized alpha-Aminocarbanions. A Novel Methodology Toward the Synthesis of 2-Aminoalcohols" Tetrahedron Lett.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Tsunoda, O. Sasaki, O. Takeuchi, and S. Ito: "An Efficient Method for Hydrolysis of N-Monosubstituted Amides Utilization of Intramolecular N-O Acyl Migration in Hydroxypivalimides" Tetrahedron.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S. Lai, Y. Shizuri, S. Yamamura, K. Kawai, Y. Terada, and H. Furukawa: "New Metabolites of Two Hybrid Strains ME 0004 and 0005 Derived from Penicillium Citreo-Viride B. IFO 6200 and 4692" Chemistry Lett.589-692 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H. Shigemori, N. Sakai, E. Miyoshi, Y. Shizuri, and Y. Yamamura: "Bioactive Substances from Lespedeza cuneata L. G. Don and their Biological Activities" Tetrahedron. 46. 383-394 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S. Lai, K. Matsunaga, Y. Shizuri, and S. Yamamura: "Biomimetic Synthesis of Citreoviridin-type Compounds and Isolation of Epicitreoviridinol, a New Metabolite of Penicillium Pedemontanum IFO 9583" Tetrahedron Lett.31. 5503-5506 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shizuri, S. Maki, M. Ohkubo, and S. Yamamura: "Synthesis of(+)-Pentalenene using Electrochemical Method as a Key Step" Tetrahedron Lett.31. 7167-7168 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] A. Ishikawa, H. Uchiyama, T. Katsuki, and M. Yamaguchi: "Stereoelectronically Controlled [2, 3]Wittig Rearrangement of Isopropyl 2'-Heterosubstituted-2'-alkenyloxyacetates" Tetrahedron Lett.31. 2415-2418 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] A. Ishikawa, Y. Ito, and T. Katsuki: "Kinetic Resolution of dl-2, 3-Epoxy Alcohols with Chiral Titanium Complex Bearing Norephedrin Derived Ligand" Tetrahedron Lett.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] A. Fukuzawa, Mya Aye, M. Nakamura, M. Tamura, and A. Murai: "Biosynthetic Formation of Cyclic Bromo-ethers Initiated by Lactoperoxidase" Chemistry Lett.1287-1290 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] A. Fukuzawa, Mya Aye, M. Nakamura, M. Tamura, and A. Murai: "Structure Elucidation of Laureoxanyne, A New Nonisoprenoid C_<15> Enyne, Using Lactoperoxidase" Tetrahedron Lett.31. 4895-4898 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] A. Fukuzawa, Mya Aye, and A. Murai: "A Direct Enzymatic Synthesis of Laurencin from Laurediol" Chemistry Lett.1579-1580 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] A. Fukuzawa, Mya Aye, Y. Takaya, T. Masamune, and A. Murai: "A Sesquiterpene Alcohol from the Red Alga Laurencia Nipponica" Phytochemistry. 29. 2337-2339 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K. Tsushima and A. Murai: "Conversion of 2-Heptenolides into Substituted Oxocene System. Its Application to the Synthesis of(+)- Lauchisan" Chemistry Lett.761-764 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] A. Fukuzawa, M. Kusunoki, and A. Murai: "Synthesis of the C/D Ring Analogue of Glycinoeclepin A" Chemistry Lett.

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

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Published: 1993-08-12  

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