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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)
丹羽 治樹  名古屋大学, 理学部, 助教授 (20135297)
野老山 喬  大阪市立大学, 理学部, 教授 (90046938)
柿澤 寛  筑波大学, 化学系, 教授 (50015492)
高杉 光雄  北海道大学, 理学部, 教授 (70000833)
Project Period (FY) 1988 – 1990
Project Status Completed (Fiscal Year 1990)
Budget Amount *help
¥15,300,000 (Direct Cost: ¥15,300,000)
Fiscal Year 1990: ¥4,000,000 (Direct Cost: ¥4,000,000)
Fiscal Year 1989: ¥4,300,000 (Direct Cost: ¥4,300,000)
Fiscal Year 1988: ¥7,000,000 (Direct Cost: ¥7,000,000)
KeywordsGlycinoeclepin A / Biosynthesis / Biogenetic Pathway / Biorhythm / Active Substance / Polyprenol / Palytoxin / Intramolecular Stacking / 酵素 / 就眠運動 / 生合成前駆体合成 / 花色素
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).

Report

(4 results)
  • 1990 Annual Research Report   Final Research Report Summary
  • 1989 Annual Research Report
  • 1988 Annual Research Report
  • Research Products

    (230 results)

All Other

All Publications (230 results)

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

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      1990 Final Research Report Summary
  • [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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  • [Publications] Y.Hirata,D.Uemura,Y.Ohizumi: "Handbook of Natural Toxins Vol.3" A.T.Tu, 241---258 (1988)

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  • [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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  • [Publications] D.Uemura: "Bioorganic Marine Chemistry" P.J.Scheuer, 1---31 (1991)

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  • [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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      1990 Final Research Report Summary
  • [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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      1990 Final Research Report Summary
  • [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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      1990 Final Research Report Summary
  • [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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      1990 Final Research Report Summary
  • [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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      1990 Final Research Report Summary
  • [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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      1990 Final Research Report Summary
  • [Publications] K. Monde, K. Sasaki, A. shirata, and M. Takasugi: "Brassicanal C and Two Dioxindoles from Brassica oleracea var. capitata" Phytochemistry.

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      1990 Final Research Report Summary
  • [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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      1990 Final Research Report Summary
  • [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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      1990 Final Research Report Summary
  • [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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      1990 Final Research Report Summary
  • [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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      1990 Final Research Report Summary
  • [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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      1990 Final Research Report Summary
  • [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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      1990 Final Research Report Summary
  • [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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  • [Publications] K. Fujiwara, H. Sakai, and M. Hirama: "Enyn[3]cumulene. Synthesis and Mode of Aromatization" J. Org. Chem.

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  • [Publications] T. oishi, M. Hirama, L. R. Sita, and S. Masamune: "Synthesis of Chiral 2, 2'-Bipyrrolidine Derivatives" Synthesis.

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  • [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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      1990 Final Research Report Summary
  • [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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      1990 Final Research Report Summary
  • [Publications] S. Ohnuma, T. Koyama, and K. Ogura: "Enzymatic Synthesis of Glycinoprenols" Tetrahedron Lett.32. 241-242 (1991)

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      1990 Final Research Report Summary
  • [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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  • [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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  • [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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      1990 Final Research Report Summary
  • [Publications] T. Ohta, S. Shiokawa, R. Sakamoto, and S. Nozoe: "Diastereospecific Synthesis of (-)-Statine" Tetrahedron Lett.31. 7329-7332 (1990)

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      1990 Final Research Report Summary
  • [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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  • [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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  • [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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  • [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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  • [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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  • [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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  • [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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  • [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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  • [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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  • [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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  • [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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  • [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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  • [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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  • [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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  • [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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  • [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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  • [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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  • [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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  • [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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  • [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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  • [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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  • [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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  • [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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  • [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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  • [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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  • [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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      1990 Final Research Report Summary
  • [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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  • [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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  • [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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  • [Publications] T. Suga and T. Endo: "Geranyl Diphosphate Synthase in Leaves of Pelagronium roseum" Phytochemistry.

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    • Related Report
      1990 Final Research Report Summary
  • [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.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [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)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [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)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [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
    • Related Report
      1990 Final Research Report Summary
  • [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
    • Related Report
      1990 Final Research Report Summary
  • [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
    • Related Report
      1990 Final Research Report Summary
  • [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
    • Related Report
      1990 Final Research Report Summary
  • [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
    • Related Report
      1990 Final Research Report Summary
  • [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
    • Related Report
      1990 Final Research Report Summary
  • [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
    • Related Report
      1990 Final Research Report Summary
  • [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
    • Related Report
      1990 Final Research Report Summary
  • [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
    • Related Report
      1990 Final Research Report Summary
  • [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
    • Related Report
      1990 Final Research Report Summary
  • [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
    • Related Report
      1990 Final Research Report Summary
  • [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
    • Related Report
      1990 Final Research Report Summary
  • [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
    • Related Report
      1990 Final Research Report Summary
  • [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
    • Related Report
      1990 Final Research Report Summary
  • [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
    • Related Report
      1990 Final Research Report Summary
  • [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
    • Related Report
      1990 Final Research Report Summary
  • [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
    • Related Report
      1990 Final Research Report Summary
  • [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
    • Related Report
      1990 Final Research Report Summary
  • [Publications] K.Hayano,H.Shirahama,and T.Matsumoto: "A Cyclopropane Sliding Reaction of △^3ーAfricanー10ーy1 Cation" Bull.Chem.Soc.Jpn.63. 628-629 (1990)

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      1990 Annual Research Report
  • [Publications] M.Hashimoto,T.Kan,K.Nozaki,M.Yanagiya,H.Shirahama,and T.Matsumoto: "Total Synthesis of (+)ーThyrsiferol,(+)ーThyrsiferolー23 Acetate,and (+)ーVenustatriol" J.Org.Chem.55. 5088-5107 (1990)

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      1990 Annual Research Report
  • [Publications] M.Hashimoto,H.Harigaya,M.Yanagiya,H.Shirahama: "Total Synthesis of the mesoーTriterpene Polyether Teurilene" J.Org.Chem.

    • Related Report
      1990 Annual Research Report
  • [Publications] K.Monde,N.Katsui,A.Shirata,and M.Takasugi: "Brassicanals A and B,Novel SulfurーContaining Phytoalexins from the Chinese Cabbage <Brassica>___ー <campestris>___ー L.ssp.<pekinensis>___ー" Chemistry Lett.209-210 (1990)

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      1990 Annual Research Report
  • [Publications] K.Monde,K.Sasaki,A.Shirata,and M.Takasugi: "4ーMethoxybrassinin,a SulphurーContaining Phytoalexin from <Brassica>___ー <oleracea>___ー" Phytochemistry. 29. 1499-1500 (1990)

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      1990 Annual Research Report
  • [Publications] K.Monde,M.Takasugi,J.A.Lewis,and G.R.Fenwick: "TimeーCourse Studies of Phytoalexins and Glucosinolates in UVーIrradiated Turnip Tissue" Z.Naturforsch.,C.

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      1990 Annual Research Report
  • [Publications] K.Monde,K.Sasaki,A.Shirata,and M.Takasugi: "Brassicanal C and Two Dioxindoles from <Brassica>___ー <oleracea>___ー var.<capitata>___ー" Phytochemistry.

    • Related Report
      1990 Annual Research Report
  • [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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      1990 Annual Research Report
  • [Publications] K.Monde,K.Sasaki,A.Shirata,and M.Takasugi: "Methoxybrassinins A and B,Two SulphurーContaining Stress Metabolites from <Brassica>___ー <oleracea>___ー" Phytochemistry.

    • Related Report
      1990 Annual Research Report
  • [Publications] T.Suzuki,O.Sato,and M.Hirama: "Two Diverse Modes of Aromatization of a New 10ーMembered Ring Analogue of Neocarzinostatin Chromophore" Tetrahedron Lett.31. 4329-4332 (1990)

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      1990 Annual Research Report
  • [Publications] T.Suzuki,O.Sato,and M.Hirama: "Palladium Catalyzed Stereospecific Cyclization of Hydroxy Epoxides.Stereocontrolled Synthesis of Cisーand Transー2ーalkenylー3ーhydroxytetrahydropyrans" Tetrahedron Lett.31. 4747-4750 (1990)

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      1990 Annual Research Report
  • [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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      1990 Annual Research Report
  • [Publications] 藤原 憲秀,平間 正博: "ビラジカルを発生する抗腫瘍性天然物とモデルの化学" Chemistry Today. 232. 14-21 (1990)

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      1990 Annual Research Report
  • [Publications] 大石 徹,平間 正博: "2,2'ービピロリジン型配位子を用いる不斉オスミン酸酸化" 有機合成化学協会誌. 48. 1006-1007 (1990)

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      1990 Annual Research Report
  • [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.

    • Related Report
      1990 Annual Research Report
  • [Publications] M.Hirama,T.Noda,S,Yasuda,and S.Ito: "Simple Strategy for the Synthesis of the AvermectinーMilbemycin Family.Total Synthesis of Milbemycin α1" J.Am.Chem.Soc.

    • Related Report
      1990 Annual Research Report
  • [Publications] K.Fujiwara,H.Sakai,and M.Hirama: "Enyn〔3〕cumulene.Synthesis and Mode of Aromatization" J.Org.Chem.

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      1990 Annual Research Report
  • [Publications] T.Oishi,M.Hirama,L.R.Sita,and S.Masamune: "Synthesis of Chiral 2,2'ーBipyrrolidine Derivatives" Synthesis.

    • Related Report
      1990 Annual Research Report
  • [Publications] M.Kitaoka,H.Nagaki,T.Kinoshita,M.Kuribayashi,T.Koyama,and K.Ogura: "Negative Ion Fast Atom BombardmentーTandem Mass Spectrometry for Structural Analysis of Isoprenoid Diphosphates" Anal.Biochem.185. 182-186 (1990)

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      1990 Annual Research Report
  • [Publications] K.Koyama,H.Inoue,S.Ohnuma,and K.Ogura: "Prenyltransferase Reaction Involving Enantiomeric DiscriminationーーーEnzymatic Synthesis of (S)ー10,11ーEpoxyーfarnesol from Racemic 6,7ーEpoxyfarnesol Diphosphate and Isopentenyl Diphosphate" Tetrahedron Lett.31. 4189-4190 (1990)

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      1990 Annual Research Report
  • [Publications] S.Ohnuma,T.Koyama,and K.Ogura: "Enzymatic Synthesis of Glycinoprenols" Tetrahedron Lett.32. 241-242 (1990)

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      1990 Annual Research Report
  • [Publications] H.Sagami,S.Matsuoka,and K.Ogura: "Formation of Z__ー,E__ー,E__ーーGeranylgeranyl Diphosphate by Rat Liver Microsomes" J.Biol.Chem.

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      1990 Annual Research Report
  • [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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      1990 Annual Research Report
  • [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

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      1990 Annual Research Report
  • [Publications] T.Ohta,S.Shiokawa,R.Sakamoto,and S.Nozoe: "Diastereospecific Synthesis of (ー)ーStatine" Tetrahedron Lett.31. 7329-7332 (1990)

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      1990 Annual Research Report
  • [Publications] T.Ohta,S.Shiokawa,E.Iwashita,N.Sato,and S.Nozoe: "Synthesis of (2S,3S)ー3ーHydroxypyroglutamate and Its Application to Carbapenem Synthesis" J.Org.Chem.

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      1990 Annual Research Report
  • [Publications] I.Shimada,Y.Maki,and H.Sugiyama: "Nー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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      1990 Annual Research Report
  • [Publications] M.O.Ishitsuka,T.Kusumi,A.Ichikawa,and H.Kakisawa: "Bicyclic Diterpenes from Two Species of Brown Algae opf the Dictyotaceae" Phytochemistry. 29. 2605-2610 (1990)

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      1990 Annual Research Report
  • [Publications] S.Seo,A.Uomori,Y.Yoshimura,H.Seto,Y.Ebizuka,H.Noguchi,U.Sankawa,and K.Takeda: "Biosynthesis of Isofucosterol from [2ー^<13>C^2H3]Acetate and [1,2ー^<13>C_2]Acetate in Tissue Cultures of <Physalis>___ー <peruviana>___ーーThe Stereochemistry of the Hydride Shift from Cー24 to Cー25" J.Chem.Soc.,Perkin Trans I. 105-109 (1990)

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      1990 Annual Research Report
  • [Publications] U.Sankawa,H.Noguchi,T.Hashimoto,and Y.Yamada: "Nonーstereospecific Incorporation of (1,2ー^<13>C_2)ーAcetate into Tropane Alkaloids in <Hyscyamus>___ー <albus>___ー" Chem.Pharm.Bull.38. 2066-2068 (1990)

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      1990 Annual Research Report
  • [Publications] T.Hakamatsuka,H.Noguchi,Y.Ebizuka,and U.Sankawa: "Isoflavone Synthase from Cell Suspension Cultures of <Pueralia>___ー <lobata>___ー" Chem.Pharm.Bull.38. 1942-1945 (1990)

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      1990 Annual Research Report
  • [Publications] M.F.Hashim,T.Hakamatsuka,Y.Ebizuka,and U.Sankawa: "Reaction Mechanism of Oxidative Rearrangement of Flavone in Isofalvone Biosynthesis" FEBS Letters. 271. 219-222 (1990)

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      1990 Annual Research Report
  • [Publications] K.Ichinose,M.Sugimori,A.Itai,Y.Ebizuka,and U.Sankawa: "Stable Ketoーtautomerism of Tetrahydroxynaphthalene in in Alkali:Theoretical Support to the PostーAromatic Reduction in the Biosynthesis of Aromatic Polyketides" Tetrahedron Lett.31. 5905-5908 (1990)

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      1990 Annual Research Report
  • [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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      1990 Annual Research Report
  • [Publications] N.Yamauchi and K.Kakinuma: "Biochemical Studies on 2ーDeoxyー<scyllo>___ーーinosose Formation in the 2ーDeoxystreptamine Biosynthesis.1.Facile Chemical Preparation of 2ーDeoxyー<scyllo>___ーーinosose" J.Antibiot.

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      1990 Annual Research Report
  • [Publications] N.Yamauchi,Y.Fujimoto,and K.Kakinuma: "Biochemical Studies on 2ーDeoxyー<scyllo>___ーーinosose Formation in the 2ーDeoxystreptamine Biosynthesis.2.Quantitative Analysis of 2ーDeoxyー<scyllo>___ーーinosose" J.Antibiot.

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      1990 Annual Research Report
  • [Publications] N.Yamauchi,K.Kakinuma,K.Shimotono,and T.Endo: "Biochemical Studies on 2ーDeoxyー<scyllo>___ーーinosose Formation in the 2ーDeoxystreptamine Biosynthesis.3.<In>___ー <vitro>___ー Synthesis of 2ーDeoxyー<scyllo>___ーーinosose with the cellーfree extract of <Streptomyces>___ー <fradiae>___ー" J.Antibiot.

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      1990 Annual Research Report
  • [Publications] S.Nishiwaki,H.Fujiki,M.Suganuma,H.FuruyaーSuguri,Y.Iida,M.Ojika,K.Yamada,D.Uemura,F.J.Schmitz,and T.Sugimura: "Estimation of Tumor Promoting Activity ans Structureーfunction Relationship of Okadaic Acid Derivatives" Carcinogenesis. 11. 1837-1841 (1990)

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      1990 Annual Research Report
  • [Publications] S.M.Ward,F.Vogalis,D.P.Blondfield,H.Ozaki,N.Fusetani,D.Uemura,N.G.Publicover,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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      1990 Annual Research Report
  • [Publications] D.Uemura,T.Chiba,Y.Hayashi,and J.Aiso: "Cytotoxic Alkaloids from the Marine Sponges" J.Nat.Prod.

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      1990 Annual Research Report
  • [Publications] A.Carl,D.Uemura,N.Fusetani,and K.M.Sanders: "Modulation of Ca^<2+>ーActivated K^+ Channels by Protein Kinase A and Phosphatase Inhibitors" Am.J.Physiol.

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      1990 Annual Research Report
  • [Publications] T.Kondo,K.Oki,K.Yoshida,and T.Goto: "Structure of Violdelphin,an Anthocyanin from Violet Flower of <Delphinium>___ー <hydridum>___ー" Chemistry Lett.137-138 (1990)

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      1990 Annual Research Report
  • [Publications] T.Goto,K.Yoshida,M.Yoshikane,and T.Goto: "Chiral Stacking of a Natural Flavone,Flavocommelin,in in Aqueous Solutions" Tetrahedron Lett.31. 713-716 (1990)

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      1990 Annual Research Report
  • [Publications] K.Yoshida,T.Kondo,K.Kameda,and T.Goto: "Structure of Anthocyanins Isolated from Purple Leaves of <Perilla>___ー <ocimoides>___ー L.var.<crispa>___ー Benth and Their Isomerization by Irradiation of Light" Agric.Biol.Chem.54. 1745-1751 (1990)

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      1990 Annual Research Report
  • [Publications] T.Hoshino and T.Goto: "Effects of pH and Concentration on the SelfーAssociation of Malvin Quinonoidal BaseーーーElectronic and Circular Dichroic Studies" Tetrahedron Lett.31. 1593-1596 (1990)

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      1990 Annual Research Report
  • [Publications] T.Kondo,M.Ueda,and T.Goto: "Structure of Ternatin Bl,A Pentacylated Anthocyanin Substituted on the Bーring Asymmetrically with Two Long Chains" Tetrahedron. 46. 4749-4756 (1990)

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      1990 Annual Research Report
  • [Publications] T.Goto and T.Kondo: "Struktur und Molekulare Stapelung von AnthocyanenーーーVariation der Blufenfarben" Angew.Chem.10. 17-33 (1991)

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      1990 Annual Research Report
  • [Publications] T.Goto and T.Kondo: "Structure and Molecular Stacking of AnthocyaninsーーーFlower Color Variation" Angew.Chem.Int.Ed.Eng.30. 17-33 (1991)

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      1990 Annual Research Report
  • [Publications] H.Niwa,T.Ogawa,and K.Yamada: "Stereoselective Synthesis of (ー)ーTrachelanthic Acid and (+)ーViridiforic Acid,Necic Acids Components of Pyrrolizidine Alkaloids from a Common Intermediate" Bull.Chem.Soc.Jpn.63. 3707-3709 (1990)

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      1990 Annual Research Report
  • [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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      1990 Annual Research Report
  • [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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      1990 Annual Research Report
  • [Publications] T.Tikoroyama,Y.Kotsuji,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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      1990 Annual Research Report
  • [Publications] T.Tokuyama,T.Tsujita,H.M.Garraffo,T.F.Spande,and J.W.Daly: "Alkaloids from <Dendrobatid>___ー Poison Frogs:Further Pumiliotoxins and Allopumiliotoxins and a Reassignment of the Keto Function in Pumilioーtoxin 307F" Tetrahedron.

    • Related Report
      1990 Annual Research Report
  • [Publications] T.Tokuyama,T.Tsujita,A.Shimada,H.M.Garaffo,T.F.Spande,and J.W.Daly: "Alkaloids from <Dendrobatid>___ー Poison Frogs:Further cisーDecahydroquinolines and 8ーMethylindolizines" Tetrahedron.

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      1990 Annual Research Report
  • [Publications] T.Yoshioka,R.ーY.Zheng,S.Ohta,and T.Suga: "An Anomaly in the Biosynthesis of (E__ー,E__ー)ーFarnesol by the Crude Enzyme System of <Pisum>___ー <sativum>___ー" Phytochemistry. 29. 3467-3472 (1990)

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      1990 Annual Research Report
  • [Publications] Y.Hiraga,S.Izumi,T.Hirata,and T.Suga: "Facile Synthesis of Regioselective Deuteriated (3R__ー)ー(ー)ー[8,8,8ー^2H_3]Linalool" Chemistry Lett.49-52 (1990)

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      1990 Annual Research Report
  • [Publications] T.Suga and T.Endo: "Geranyl Diphosphate Synthase in Leaves of <Pelagronium>___ー roseum" Phytochemistry.

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      1990 Annual Research Report
  • [Publications] S.Izumi,M.Aihara,Y.Hiraga,T.Hirata,and T.Suga: "Synthesis of [10,10,10ー^2H_3]Geranyl Diphosphate" J.Labelled Compd.Radiopharm.

    • Related Report
      1990 Annual Research Report
  • [Publications] S.Izumi,D.I.Ito,T.Hirata,and T.Suga: "The Facilitation of the Diphosphate Group Elimination from Geranyl Diphosphate by Chelation of Magnesium Ion in the Cyclic Monoterpenoid Biosynthesis" Tetrahedron Lett.

    • Related Report
      1990 Annual Research Report
  • [Publications] T.Tsunoda,O.Sasaki,and S.Ito: "AzaーClaisen Rearrangement of Amide Enolates.Stereoーselective Synthesis of 2,3ーDisubstituted Carboxamides" Tetrahedron Lett.31. 727-730 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] T.Tsunoda,O.Sasaki,and S.Ito: "An Efficient Method for Hydrolysis of NーMonosubstituted Amides via Acetoxypivalimides" Tetrahedron Lett.31. 731-734 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] S.Ito and T.Tsunoda: "A Few New Methods for Asymmetric Synthesis" Pure & Appl.Chem.62. 1405-1408 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] R.B.Woodward,W.A.Ayer,J.M.Beaton,F.Bickelhaupt,R.Bonnett,P.Buchschacher,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)

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      1990 Annual Research Report
  • [Publications] M.Nishizawa,H.Yamada,J.Sano,S.Ito,Y.Hayashi,H.Ikeda,C.M.Shiro,and H.Tokuda: "Structure of Syzygiol:A SkinーTumor Promotion Inhibitor" Tetrahedron Lett.32. 211-212 (1991)

    • Related Report
      1990 Annual Research Report
  • [Publications] M.Hirama,T.Noda,S.Yasuda,and S.Ito: "Simple Strategy for the Synthesis of the AvermectinーMilbemycin Family.Total Synthesis of Milbemycin α_1" J.Am.Chem.Soc.

    • Related Report
      1990 Annual Research Report
  • [Publications] T.Tsunoda,K.Fujiwara,Y.Yamamoto,and S.Ito: "SiteーSpecific Generation of Nonstabilized αーAminocarbanions.A Novel Methodology Toward the Synthesis of 2ーAminoalcohols" Tetrahedron Lett.

    • Related Report
      1990 Annual Research Report
  • [Publications] T.Tsunoda,O.Sasaki,O.Takeuchi,and S.Ito: "An Efficient Method for Hydrolysis of NーMonosubstituted Amides Utilization of Intramolecular NーO Acyl Migration in Hydroxypivalimides" Tetrahedron.

    • Related Report
      1990 Annual Research Report
  • [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ーviride B.IFO 6200 and 4692" Chemistry Lett.589-592 (1990)

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      1990 Annual Research Report
  • [Publications] H.Shigemori,N.Sakai,E.Miyoshi,Y.Shizuri,and S.Yamamura: "Bioactive Substances from Lespedeza cuneata L.G.Don and Their Biological Activities" Tetrahedron. 46. 383-394 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] S.Lai,K.Matsunaga,Y.Shizuri,and S.Yamamura: "Biomimetic Synthesis of Citreoviridinーtype Compounds and Isolation of Epicitreoviridinol,a New Metabolite of Penicillium Pedemontanum IFO 9583" Tetrahedron Lett.31. 5503-5506 (1990)

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      1990 Annual Research Report
  • [Publications] Y.Shizuri,S.Maki,M.Ohkubo,and S.Yamamura: "Synthesis of (±)ーPentalenene Using Electrochemical Method as a Key Step" Tetrahedron Lett.31. 7167-7168 (1990)

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      1990 Annual Research Report
  • [Publications] A.Ishikawa,H.Uchiyama,T.Katsuki,and M.Yamaguchi: "Stereoelectronically Controlled [2,3]Wittig Rearrangement of Isopropyl 2'ーHeterosubstitutedー2'ーalkenyloxyacetates" Tetrahedron Lett.31. 2415-2418 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] A.Ishikawa,Y.Ito,and T.Katsuki: "Kinetic Resolution of d1ー2,3ーEpoxy Alcohols with Chiral Titanium Complex Bearing Norephedrin Derived Ligand" Tetrahedron Lett.

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      1990 Annual Research Report
  • [Publications] A.Fukuzawa,Mya Aye,M.Nakamura,M.Tamura,and A.Murai: "Biosynthetic Formation of Cyclic Bromoーethers Initiated by Lactoperoxidase" Chemistry Lett.1287-1290 (1990)

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      1990 Annual Research Report
  • [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)

    • Related Report
      1990 Annual Research Report
  • [Publications] A.Fukuzawa,Mya Aye,and A.Murai: "A Direct Enzymatic Synthesis of Laurencin from Laurediol" Chemistry Lett.1579-1580 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] A.Fukuzawa,Mya Aye,Y.Takaya,T.Masamune,and A.Murai: "A Sesquiterpene Alcohol from the Red Alga <Laurencia>___ー <nipponinca>___ー" Phytochemistry. 29. 2337-2339 (1990)

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      1990 Annual Research Report
  • [Publications] K.Tsushima and A.Murai: "Conversion of 2ーHeptenolides into Substituted Oxocene System.Its Application to the Synthesis of (+)ーLauchisan" Chemistry Lett.761-764 (1990)

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      1990 Annual Research Report
  • [Publications] A.Fukuzawa,M.Kusunoki,and A.Murai: "Synthesis of the C/D Ring Analogue of Glycinoeclepin A" Chemistry Lett.

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      1990 Annual Research Report
  • [Publications] F.Matsuda and H.Shirahama: "Chemistry of ThreeーDimensional Polycyclic Molecules" E.Osawa and O.Yonemitsu,

    • Related Report
      1990 Annual Research Report
  • [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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      1990 Annual Research Report
  • [Publications] Y.Hirata,D.Uemura,and Y.Ohizumi: "Handbook of Natural Toxins Vol.3" A.T.Tu, 241---258 (1988)

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      1990 Annual Research Report
  • [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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      1990 Annual Research Report
  • [Publications] D.Uemura: "Bioorganic Marine Chemistry" P.J.Scheuer, 1---31 (1991)

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      1990 Annual Research Report
  • [Publications] M.Takasugi: "Brassicanals A and B,Novel Sulfur-containing Phytoalexins from the Chinese Cabbage Brassica compestris L.ssp.pekinensis" Chemistry Letters. 209-210 (1990)

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      1989 Annual Research Report
  • [Publications] M.Takasugi: "4-Methoxybrassinin,a Sulfur-containing Phytoalexin from Brassica oleraces" Phytochemistry.

    • Related Report
      1989 Annual Research Report
  • [Publications] K.Ogura: "Protection of Hexaprenyl Diphosphate Synthase of Micrococcus luteus B-P 26 against Inactivation by Sulphydryl Reagents and Arginine-specific Reagents" Biochem.Biophys.Acta. 995. 138-143 (1989)

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      1989 Annual Research Report
  • [Publications] K.Ogura: "The Biosynthesis of Dehydrolichyl Phosphates by Rat Liver Microsomes" Biochem.Biophys.Acta. 1002. 218-224 (1989)

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      1989 Annual Research Report
  • [Publications] K.Ogura: "Artificially Elicited Capabilities of Enzymes and Their Application in Natural Product Chemistry" Pure Apple.Chem.61. 477-480 (1989)

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      1989 Annual Research Report
  • [Publications] K.Ogura: "Formation of a Stable and Catalytically Active Complex of the Two Essential Components of Hexaprenyl Diphoshphate synthese from Micrococcus luteus B-P26" Biochem.Biophys.Res.Commun.160. 448-452 (1989)

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      1989 Annual Research Report
  • [Publications] K.Ogura: "Undecaprenyl Diphoshate Synthase Reaction with Artificial Substrate Homelogues---Novel Behavior in the Termination of Prenyl Chain Elongation" Tetrahedron. 45. 6145-6160 (1989)

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      1989 Annual Research Report
  • [Publications] K.Ogura: "Kinetic Studies on th Prenyl Chain Elongation by Undecaprenyl Diphosphate Synthase with Artificial Substrate Homologues" FEBS Let.257. 71-74 (1989)

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      1989 Annual Research Report
  • [Publications] S.Nozoe: "Chirospecific Synthesis of Amino Acids and Analogues" Amino Acids.

    • Related Report
      1989 Annual Research Report
  • [Publications] S.Nozoe: "Synthesis of (3S,5R)-Carbapenam-3-carboxylate" J.Chem.soe.,chem.Commun.

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      1989 Annual Research Report
  • [Publications] Y.Maki: "N-acylation of stimulatory amino acids changes chiral recognition of the flesh fly labellar sugar site" J.compt.Physiol.,A. 165. 193-196 (1989)

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      1989 Annual Research Report
  • [Publications] Y.Maki: "Farnesyl Diphosphate Synthetase Reaction of Articifial Substrates with Oxygen" Chemistry Letters.

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      1989 Annual Research Report
  • [Publications] H.Kakisawa: "Absolute Configuration of Marine Diterpenes Possessing a Xenicane Skeleton" Tetrahedron Letters. 30. 3147-3150 (1989)

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      1989 Annual Research Report
  • [Publications] H.Kakisawa: "The Absolute Configuration at 8- and 9-Carbons of Adda, an Amino Acid Component of Hepatotoxin,Cyanoviridin RR" Tetrahedron Letters. 30. 4245-4248 (1989)

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      1989 Annual Research Report
  • [Publications] U.Sankawa: "Nonstereospecific Proton Removal in the Enzymatic Formation of Orsellinic Acid from Chiral Malonate" J.Am.Chem.Soc.111. 5498-5500 (1989)

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      1989 Annual Research Report
  • [Publications] A.Kawaguchi: "Binding site of Cerulenin in fatty acid synthetase" J.Biochem.105. 751-755 (1989)

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      1989 Annual Research Report
  • [Publications] Y.Shizuri: "Potasium Lespedezate and Potassium Isolespedezate,Bioactive Substances concerned with Circadian Rhythem in Nyctinastic Plants" Tetrahedron Letters. 30. 3991-3994 (1989)

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      1989 Annual Research Report
  • [Publications] Y.Shizuri: "Total Syntheses of Potassium Lespedezate and Potassium Isolespedezate,Bioactive Substances Concerned with Circadian Rhythm in Nyctinastic Plants" Tetrahedron Letters. 30. 6389-6392 (1989)

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      1989 Annual Research Report
  • [Publications] Y.Shizuri: "Bioactive Substances from Lespedeza Cuneata L.G.Don and Their Biological Activities" Tetrahedron. 46. 383-394 (1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] D.Uemura: "Structure-Activity Studies of the Nonphorbol Tumor Promoter Palytoxin in Swiss 3T3 Cells" Cancer Res.49. 5837-5842 (1989)

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      1989 Annual Research Report
  • [Publications] T.Goto: "Structure of Anthocyanins in Scarlet,Purple, and Blue Flowers of Salvia" Tetrahedron Lettrs. 30. 6729-6732 (1989)

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      1989 Annual Research Report
  • [Publications] T.Goto: "Structure of Lobel-nin A and B,Novel Anthocyanins Acylated with Three and Four Different Organic Acids,Respectively" Tetrahedron Lettrs. 30. 6055-6058 (1989)

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      1989 Annual Research Report
  • [Publications] T.Goto: "Structure of Malonylshisonin,a Genuine Pigment in Purple Leaves of Perilla ocimoides L.var.crispa Benth" Agric.Biol.Chem.53. 797-800 (1989)

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      1989 Annual Research Report
  • [Publications] H.Niwa: "An Efficient Enantioselective Synthesis of(+)-Indicine N-Oxide,an Antitumor Pyrrolizidine Alkaloid" Tetrahedron Letters. 30. 4985-4986 (1989)

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      1989 Annual Research Report
  • [Publications] 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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      1989 Annual Research Report
  • [Publications] T.Tokoroyama: "Synthetic Studies on Terpenoid compounds Part 27.Total Synthesis of Calodendrolide" J.Chem.Soc.,Chem.Commun.

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      1989 Annual Research Report
  • [Publications] T.Tokuyama: "Alkaloids from Dendrobatid Poison Frogs:Further(allo)-pumiliotoxins and a Ressignment of the Keto Function in Pumiliotoxin 307F" Tetrahedron.

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      1989 Annual Research Report
  • [Publications] T.Suga: "Glycinoprenols:Novel Polyprenols Possessing a.Phythyl Residue from the Leaves of Soybean" J.Org.chem. 54. 3390-3393 (1989)

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      1989 Annual Research Report
  • [Publications] T.Suga: "Sesquiterpene Glycosides and other Terpene Constituents from the Flowers of Pittosporum Tobira" Phytochemistry. 28. 3085-3091 (1989)

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      1989 Annual Research Report
  • [Publications] T.Suga: "Synthesis of 4- and 5-Regioselectively Deuterated Geranyl Diphosphates" J.Chem.Soc.,Perkin Trans.l. 1811-1814 (1989)

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      1989 Annual Research Report
  • [Publications] S.Ito: "Azaclaisen Rearrangement of Amide Enolates.Stereoselective Syntheses of 2,3-Disubstituted Carboxamides" Tetrahedron Letters. 31. 727-730 (1990)

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      1989 Annual Research Report
  • [Publications] S.Ito: "An Efficient Method for Hydrolysis of N-Monosubstituted Amides via Acetoxypivalimides." Tetrahedron Letters. 31. 731-734 (1990)

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      1989 Annual Research Report
  • [Publications] S.Ito: "A few new Method for Asymmetric Synthesis" Pure and Appl.Chem.

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      1989 Annual Research Report
  • [Publications] T.Katsuki: "Stereoelectronically Controlled[2,3]Witting Rearrangement of Isopropyl 2'-Heterosubstituted 2'-Alkenyloxyacetates" Tetrahedron Letters.

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      1989 Annual Research Report
  • [Publications] M.Hashimoto.: Tetrahedron Letters. 29. 5947-5948 (1988)

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      1988 Annual Research Report
  • [Publications] M.Hashimoto.: Tetranhedron Letters. 29. 1143-1144 (1988)

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      1988 Annual Research Report
  • [Publications] M.Hashimoto.: Chemistry Letters. 645-646 (1988)

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      1988 Annual Research Report
  • [Publications] T.Koyama.: Phytochemistry. 27. 2005-2009 (1988)

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      1988 Annual Research Report
  • [Publications] T.Koyama.: JOURNAL OF Biochemistry. 103. 867-871 (1988)

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      1988 Annual Research Report
  • [Publications] T.Koyama.: Tetrahedron Letters. 29. 3807-3810 (1988)

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      1988 Annual Research Report
  • [Publications] T.Gotoh.: Biochem. Biophys. Res. Commun.156. 396-402 (1988)

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      1988 Annual Research Report
  • [Publications] I.Yoshida.: Biochim. Biophys. Acta.

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      1988 Annual Research Report
  • [Publications] H.Sagami.: Biochim. Biophys. Acta.

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      1988 Annual Research Report
  • [Publications] T.Ohta.: Tetrahedron Letters. 29. 4303-4304 (1988)

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      1988 Annual Research Report
  • [Publications] T.Ohta.: Tetrahedron Letters. 29. 4305-4308 (1988)

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      1988 Annual Research Report
  • [Publications] I.Shimada.: Compt. Physiol.,part A.

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      1988 Annual Research Report
  • [Publications] I.Ohtani.: Tetrahedron Letters.

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      1988 Annual Research Report
  • [Publications] I.Abe.: Chem. Pharm. Bull.36. 5031-5034 (1988)

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      1988 Annual Research Report
  • [Publications] H.Funabashi.: Journal of Biochemistry.

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      1988 Annual Research Report
  • [Publications] Y.Shizuri.: Tetrahedron Letters. 29. 1971-1974 (1988)

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      1988 Annual Research Report
  • [Publications] Y.Shizuri.: Chemistry Letters. 1419-1422 (1988)

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      1988 Annual Research Report
  • [Publications] Y.Shizuri.: Chemistry Letters. 113-116 (1989)

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      1988 Annual Research Report
  • [Publications] I.Muramatsu.: Br.J.Pharmacol.93. 811-816 (1988)

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      1988 Annual Research Report
  • [Publications] H.Ishihara.: Journal of Biological Chemistry.

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      1988 Annual Research Report
  • [Publications] H.Niwa.: Tetrahedron Letters. 29. 5139-5142 (1988)

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      1988 Annual Research Report
  • [Publications] H.Niwa.: Bull.Chem.Soc.Jpn.61. 3017-3019 (1988)

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      1988 Annual Research Report
  • [Publications] F.Toda.: Chemistry Letters. 131-134 (1988)

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      1988 Annual Research Report
  • [Publications] M.Ochiai.: J.Chem.Soc.,Chem.Commun.1076-1077 (1988)

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      1988 Annual Research Report
  • [Publications] M.Ochiai.: J.Org.Chem.53. 6144-6145 (1988)

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      1988 Annual Research Report
  • [Publications] T.Suga.: Chemistry Letters. 115-118 (1988)

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      1988 Annual Research Report
  • [Publications] T.Suga.: 日本化学雑誌. 629-634 (1988)

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      1988 Annual Research Report
  • [Publications] A.Murai.: J.Am.Chem.Soc.110. 1985-1986 (1988)

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      1988 Annual Research Report
  • [Publications] T.Kondo.: Agric.Biol.Chem.

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      1988 Annual Research Report
  • [Publications] Y.Shizuri.: "植物の化学調節" 植物化学調節学会, 32-44 (1988)

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      1988 Annual Research Report
  • [Publications] T.Goto.: "有機合成化学協会誌" 有機合成化学協会, 426-435 (1988)

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      1988 Annual Research Report
  • [Publications] T.Suga.: "有機合成化学協会誌" 有機合成化学協会, 12-21 (1988)

    • Related Report
      1988 Annual Research Report

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Published: 1988-04-01   Modified: 2016-04-21  

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