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Synthesis of Optically Active Forms of Some Useful Bioactive Substanus

Research Project

Project/Area Number 60430028
Research Category

Grant-in-Aid for General Scientific Research (A)

Allocation TypeSingle-year Grants
Research Field 製造化学・食品
Research InstitutionThe University of Tokyo

Principal Investigator

MORI Kenji  The University of Tokyo, 農学部, 教授 (20011843)

Co-Investigator(Kenkyū-buntansha) SUGAI Takeshi  The University of Tokyo, 農学部, 助手 (60171120)
KUWAHARA Shigefumi  The University of Tokyo, 農学部, 助手 (30170145)
EBATA Takashi  The University of Tokyo, 農学部, 助手 (30160378)
KITAHARA Takeshi  The University of Tokyo, 農学部, 助教授 (40087573)
Project Period (FY) 1985 – 1988
Project Status Completed (Fiscal Year 1988)
Budget Amount *help
¥21,000,000 (Direct Cost: ¥21,000,000)
Fiscal Year 1988: ¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1987: ¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1986: ¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1985: ¥15,000,000 (Direct Cost: ¥15,000,000)
Keywordsbioactive substances / synthesis / optically active compound / pheromone / insect juvenile hormone / antibiotics / natural sweetner / phytoalexin / 昆虫摂食阻害物質 / 甘味料 / 昆虫攝食阻害物質
Research Abstract

Various bioactive substances were synthesized in optically active forms. In the cace of pheromone, extensive work was executed which will be delivered as an Invited Lecture at IUPAC Congress (1989, Sweden). (1) The following pheromones were synthesized as pure enantiomer(s): serricornin, endo-brevicomin, 14-methyl-1-octadecene, stegobinone, stegobiol, invictolide, house mouse pheromone, pityol, grandisol, 1-methyl-2-cyclohexen-1-ol, tetrahydro-2,2,6-trimethyl-2H pyran-3-ol, -multistriatin, and sitophilure. These pheromone enantiomers were supplied to biologists. (2) Naturally occurring enantiomers of juvenile hormone I, II, and III were prepared. Unnatural enantiomer of juvenile hormone III was also prepared and found to be far less active (1/5240) than the natural enantiomer. (3) The following antibiotics were synthesized in optically active forms: ascochlorin, ascofuranone, zonarol, talaromycin A and B, pentalenolactone E, and trichostatin A. (4) All of the possible stereoisomers of hernandulcin, the naturally occurring sweetner, were synthesized, and only the natural one was found to be sweet. The aglycone of the sweet glycoside baiyunoside was also synthesized. The enantiomers of oryzalexins A, B, and C were synthesized. The natural enantiomers were potent as phytoalexins. (6) The enantiomers of polygodial were prepared, and both were found to be active as an insect antifeedant.

Report

(4 results)
  • 1988 Annual Research Report   Final Research Report Summary
  • 1986 Annual Research Report
  • 1985 Annual Research Report
  • Research Products

    (59 results)

All Other

All Publications (59 results)

  • [Publications] Kenji Mori;Hidenori Watanabe: Tetrahedron. 41. 3423-3428 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji Mori;Young-Bae Seu: Tetrahedron. 41. 3429-3431 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Minoru Kato;Kenji Mori: Agricultural and Biological chemistry. 49. 2479-2480 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji Mori;Takashi Ebata: Tetrahedron. 42. 4413-4420 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji Mori;Takashi Ebata: Tetrahedron. 42. 4685-4689 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji Mori;Yutaka Nakazono: Tetrahedron. 42. 6459-6464 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji Mori;Young-Bae Seu: Tetrahedron. 42. 5901-5904 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji Mori;Prapai Puapoomchareon: Liebigs Annalen der Chemie. 271-272 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji Mori;Masahiro Miyake: Tetrahedron. 43. 2229-2239 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji Mori;Braja G.Hazra;Robert J.Pfeiffer;Ashok K.Gyuta;B.S.Lindgren: Tetrahedron. 43. 2249-2254 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji Mori;Prapai Puapoomchareon: Liebigs Annalen der Chemie. 175-177 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji Mori;Young-Bae seu: Tetrahedron. 44. 1035-1038 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji Mori;Masahiro Tsuji: Tetrahedron. 44. 2835-2842 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji Mori;Koshi Koseki: Tetrahedron. 44. 6013-6020 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji Mori;Minoru Kato: Tetrahedron Letters. 27. 981-982 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji Mori;Makoto Komatsu: Tetrahedron. 43. 3409-3412 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji Mori;Michiru Waku: Tetrahedron. 41. 5653-5660 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji Mori;Hidenori Watanabe: Tetrahedron. 42. 273-281 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji, Mori; Hidenori, Watanabe: "A New Synthesis of Serricornin [(4S.6S.7S)-7-Hgdroxy-4.6-dimethyl-3-nonanone,The Sex pheromone of The Cigarette Beetle." Tetrahedvon. 41. 3423-3428 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji, Mori; Young-Bae, Seu: "Sgnthesis of Both the Enantiomers of endo-Brevicomin, the Aggregation pheromone of Oryocoetes antographus." Tetrahedvon. 41. 3429-3431 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Minoru, Kato; Kenji, Mori: "Synthesis of the Enamtiomers of 14-Methyl-1-octadecene, the Sex pheromone of the Peach Leafaniner Moth." Agrimltural and Biological chemistry.49. 2479-2480 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji, Mori; Takashi, Ebata: "Synthesis of (2S,3R,1'R)-Stegobinone, the Pheromone of the Drugatore Beetle, with Sterescontrol at C-2 and C-1'." Tetrahedron. 42. 4413-4420 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji, Mori; Takashi, Ebata: "Synthesis of (2S,3R,1'S,2'S)-Stegobiol, a New Component of the Drugstore Beetle Pheromone." Tetrahedron. 42. 4685-4689 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji, Mori; Yutaka, Nakazono: "Synthesis of Both the Enantioners of Invictolide, a Pheromone Component of the Red Imported Fire Ant." Tetrahedron. 42. 6459-6464 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji, Mori; Young-Bae, Seu: "Synthesis of Both the Enantiomers of 7-Ethyl-5-methyl-6,8-dioxabicyclo-[3,2,1]oct-3-sne, the Mus muswlus (House Mouse) Pheromone." Tetrahedron. 42. 5901-5904 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji, Mori; Prapai, Puagoomchareon: "Convesion of the Enantiomers of Sulcatol (6-Mothyl-5-hepten-2-of) to the Enantiomers of Pityol [trans-2-(1-Hydroxy-1-methylethyl)-5-methyl tetrahydsofuran], a Male Specific Attractant of the Bark Beetle Pityophthorus pithographus." Liebigs Annalen der Chemie. 271-272 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji, Mori; Masahiro, Miyake: "A New Synthesis of Both the Enantiomers of Grandisol, the Boll Weevil Pheromone." Tetrahedron. 43. 2229-2239 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji, Mori; Braja, G.Hazra; Robert J, Pfeiffer; Ashok K, Gupta; B.S, Lindgren: "Synthesis and Bioactivity of Optically Active Forms of 1-Mathyl-2-ayclohexen-1-of, an Aggregation Pheromone of Dendroctonus psendotsagae." Tetrahedron. 43. 2249-2254 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji, Mori; Prapai, Puapoomcharem: "Synthesis of the Four stercoisomers of Tetrahydro-2,2,6-trimetyl-2H-pyran-3-ol, a Volatile compound from the Eim Bark Beetle Pteleobius vittatus" Liebigs Annalen der Chemie. 175-177 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji, Mori; Young-Bae, Seu: "A New Synthesis of (-)- -Multistriatin, The pheromone of the Smaller Europian Elm Bark Beetle" Tetrahedron. 44. 1035-1038 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji, Mori; Takashi, Ebata: "Synthesis of All of the Four Possible Stereoisomers of 5-Hydroxy-4-Methyl-3-heptanone (sitophilure), the Aggregation Pheromone of the Rice Weevil and the Maise Weevil." Tetrahedron. 42. 4421-4426 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji, Mori; Hideto, Mori: "Synthesis of the Enantiomers of Juvenile Hormone" Tetrahedron. 43. 4097-4106 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji, Mori; Mitsuhiko, Fujiwara: "Synthesis of Enantiomerically Pure (10R,11S)-(+)-Juvemile Hormones and" Tetrahedron. 44. 343-354 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji, Mori; Shozo, Takechi: "Synthesis of the Natural Enantiomers of Ascochlorin, Ascofuranone and Ascofuranol." Tetrahedron. 41. 3049-3062 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji, Mori; Makoto, Komatsu: "Synthesis and Absolute Configuration of Zonarol, a Fungitoxir Hydroguinone from the Brown Seaweed Dictyopteris zonarioides." Bulletin de la Souete chimigue Belgrade. 95. 771-781 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji, Mori; Masaya, Ikumaka: "Synthesis of (-)-Talaromyurs A and B" Tetrahedron. 43. 45-58 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji, Mori; Masahiro, Tsuji: "Synthesis and Absolute Configuration of (-)-Pentalenolactone E Methyl Ester." Tetrahedron. 44. 2835-2842 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji, Mori; Koshi, Koseki: "Synthesis of Trichostatin A , a Potent Differentiation Indncer of Friend Leukemie cells, and Its Antipode." Tetrahedron. 44. 6013-6020 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji, Mori; Minoru, Kato: "Synthesis and Absolute Configuretion of (+)-Hernandulin, A New Sesguiterpene with Intensely Sweet taste." Tetrahedron Letters. 27. 981-982 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji, Mori; Makoto, Komatsu: "Synthesis of (+)-Baiyunol, the Diterpene Aglycone of the Sweet Ghycoside Baiyunoside." Tetrahedron. 43. 3409-3412 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji, Mori; Michiru, Waku: "Synthesis of Oryzalexins A, B and C, the Diterpenoidal Phytoalexins Isolated from Rice Blast Lesves Inficted with Pyricularia oryzal" Tetrahedron. 41. 5653-5660 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji, Mori; Hidenori, Watanabe: "Synthesis of Both the Enantiomers of Polygodial, An Insect Antifeedant Sesguitergene." Tetrahedron. 42. 273-281 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kenji,MORI;Masaya,IKUNAKA: Tetrahedron. 43. 45-58 (1987)

    • Related Report
      1988 Annual Research Report
  • [Publications] Kenji,MORI;Prapai,Puapoomchareon: Licbigs Annalen der Chemie. 271-272 (1987)

    • Related Report
      1988 Annual Research Report
  • [Publications] Kenji,MORI;Masahiro,MIYAKE: Tetrahedron. 43. 2229-2239 (1987)

    • Related Report
      1988 Annual Research Report
  • [Publications] K.MORI;B.G.HAZRA;R.J.Pfeiffer;A.K.GUPTA;B.S.Lindgrin: Tetrahedron. 43. 2249-2254 (1987)

    • Related Report
      1988 Annual Research Report
  • [Publications] Kenji,MORI;Makoto,KOMATSU: Tetrahedron. 43. 3409-3412 (1987)

    • Related Report
      1988 Annual Research Report
  • [Publications] Kenji,MORI;Hideto,MORI: Tetrahedron. 43. 4097-4106 (1987)

    • Related Report
      1988 Annual Research Report
  • [Publications] Kenji Mori;Hidenori Watanabe: Tetrahedron. 42. 273-281 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Kenji Mori;Yutaka Nakazono: Tetrahedron. 42. 283-290 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Kenji Mori;Takashi Ebata: Tetrahedron. 42. 4413-4420 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Kenji Mori;Takashi Ebata: Tetrahedron. 42. 4685-4689 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Kenji Mori;Minoru Kato: Tetrahedron Letters. 27. 981-982 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Kenji Mori;Makoto Komatsu: Bull.Soc Chim,Berg.95. 771-781 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Tetrahedron(Pergamon Press,U.K.). 41. 3049-3062 (1985)

    • Related Report
      1985 Annual Research Report
  • [Publications] Tetrahedron(Pergamon Press,U.K.). 41. 5653-5660 (1985)

    • Related Report
      1985 Annual Research Report
  • [Publications] Tetrahedron(Pergamon Press,U.K.). 41. 3423-3428 (1985)

    • Related Report
      1985 Annual Research Report
  • [Publications] Tetrahedron(Pergamon Press,U.K.). 41. 3429-3431 (1985)

    • Related Report
      1985 Annual Research Report
  • [Publications] Liebigs Arn.Chem.(West germany). 2083-2087 (1985)

    • Related Report
      1985 Annual Research Report

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Published: 1987-03-31   Modified: 2016-04-21  

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