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Chemical Synthesis of Pheromones of Insects, Flagellates and Mammals.

Research Project

Project/Area Number 09680576
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioorganic chemistry
Research InstitutionScience University of Tokyo

Principal Investigator

MORI Kenji  Science University of Tokyo, Department of Chemistry Professor, 理学部・第2部, 教授 (20011843)

Co-Investigator(Kenkyū-buntansha) TAKIKAWA Hirosato  Science University of Tokyo, Department of Chemistry Assistant, 理学部・第2部, 助手 (40271332)
Project Period (FY) 1997 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥3,200,000 (Direct Cost: ¥3,200,000)
Fiscal Year 1998: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 1997: ¥1,800,000 (Direct Cost: ¥1,800,000)
Keywordspheromones / optically active compounds / cymmetric synthesis
Research Abstract

1. Lurlenic acid, the female-produced pheromone of the green flagellate Chlamydomonas allensworthii, and its analogues were synthesized. Structural requirements for the expression of the pheromone activity are the sugar-part, the phenol part and the unsaturated side-chain with a polar group at its end.
2. Bark beetle pheromones such as endo-isobrevicomin, exo-isobrevicomin, bicolorin, frontalin etc. were synthesized.
3. Stegobiol and stegobinone, the drugstore beetle pheromone, were synthesized.
4. Stigmolone, the pheromone to induce the fruiting body formation of a myxobacterium Stigmatella aurantiaca, was synthesized. The natural pheromone is a racemate.
5. The racemate of the male-produced sex pheromone of the sandfly Lutzomyia longipalpis, (*)-3-methyl-alpha-himachalene and (*)-9-methylgermacrene-B, were synthesized to establish the gross structures of the pheromone components.
6. The enantiomers of 2-sec-butyl-4, 5-dihydrothiazole and (lR, 5S, 7R)-3, 4-dehydro-exo-brevicomin, the pheromone components of the house mouse Mus musculus, were synthesized.

Report

(3 results)
  • 1998 Annual Research Report   Final Research Report Summary
  • 1997 Annual Research Report
  • Research Products

    (60 results)

All Other

All Publications (60 results)

  • [Publications] Kenji Mori: "Pheromones : Syntheris and Bioactivity" Chemical Communications. 1153-1158 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kenji Mori: "Chirality and Insect Pheromones" Chirality. 10. 578-586 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kenji Mori: "Semiochemicals-Synthesis, Stereochemistry and Bioactivity" European Journal of Organic Chemistry. 1479-1489 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S.Takanashi, K.Mori: "Synthesis of Lurlenic Acid and Lurlenol, the Sex Pheromone of the Green Flagellate Chlamydomonas" Liebigs Annalen. 825-838 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S.Takanashi, K.Mori: "Synthesis of the Analogues of Lurlemic Acid with a modified Sugar pant : Chlamydomonas responds only to the D-xyluside" Liebigs Annalen. 1081-1084 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S.Takanashi, K.Mori: "Synthesis of the Analogues of Lurlent Acid with modification in the Side-chain or in the Aromatic Nucleus : Summary of the Structure-Activity Relationships" Eurupeam Journal of Organic Chemistry. 43-55 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Mori, H.Takikawa, Y.Nishimura, H.Horikiri: "Synthesis of (-)-exo-Isobrevicomin and its (-)-endo-Isomer" Liebigs Annalen. 327-332 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Yokoyama, K.Mori: "Synthesis of (1R, 1′R, 5′R, 7′R)- and (1S, 1′R, 5′R, 7′R)-1-Hydroxy-exo-brevicomin" Liebigs Annalen. 845-849 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Takikawa, S.Sano, K.Mori: "Synthesis of (1S, 2R, 5R)-Bicolorin" Liebigs Annalen. 2495-2498 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Nishimura, K.Mori: "A New Synthesis of (-)-Frontalin, the Bark Beetle Pheromone" European Journal of Organic Chemistry. 233-236 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Mori, S.Sano, Y.Yokoyama M.Bando, M.Kido: "Synthesis of Stegobiol and Its Oxidation to Stegobinone, the Components of the Female-produced Sex Pheromone of the Drugstore Beetle" European Journal of Organic Chemistry. 1135-1141 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Mori, M.Takenaka: "Synthesis of the Enantiomers of 8-Hydroxy-2,5,8-teimethyl-4-nonanone, the Myxobacterial Pheromone of Stigmatella aurantiaca" European Journal of Organic Chemistry. 2181-2184 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Domon, K.Mori: "Simple synthesis of (±)-Stigmolone(8-Hydroxy-2,5,8-teimethy 4-nonanone), the Pheromone of Stigmatella aurantiaca" European Journal of Organic Chemistry. (印刷中). (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] J.G.C.Hamilton, A.M.Hooper K.Mori, J.A.Pickett, S.Sano: "3-methyl-α-himachalene confirmed and the relative stereochemistry defined, by synthesis as the sex pheronone of the sandfly" Chemical Communications. (印刷中). (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S.Sano, K.Mori: "Synthesis of (1R^*, 3R^*, 7R^*)-3-Methyl-α-himachalene, the Racemate of the Male-produced Sex Pheromone of the Sandfly" European Journal of Organic Chemistry. (印刷中). (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S.Muto, Y.Nishimura, K.Mori: "Synthesis of Germacrene-B and Its Extension to the Synthesis of (±)-9-Methyl germacrenl-B, the Racemate of the male-Produced Sex Pheromone of the Sandfly" European Journal of Organic Chemistry. (印刷中). (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Tashiro, K.Mori: "Synthesis of the Enantiomers of 2-sec-Butyl-4,5-dihydrothiazole and (1R, 5S, 7R)-3,4-Dehydro-exo-brevicomin, the Pheromone Components of the Male Mouse" European Journal of Organic Chemistry. (印刷中). (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kenji Mori(J.G.Millar, K.F.Haynes編): "Methods in Chemical Ecology Volume1 Chapter8 : Separation of Enantiomers and Determination of Alisolute Configuration" Kluwer Academic Publishers, 350(295-338) (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kenji Mori(N.Kurihara, J.Miyamoto編): "Chirality in Agrochemicals Chapter 6 : Cherality in Insect Juvenile Hormones and Pheromones" John Wiley & Sons, 269(199-257) (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kenji Mori(Kenji Mori編): "Comprehensiue Natural Products Chemistry, Vol.8 Chapter1 : Overview" Elsevier Science Ltd., 749(1-18) (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Shin-ichi Takanashi and Kenji Mori, Pheromone Synthesis, CLXXIX.: "Synthesis of Lurlenic Acid and Lurlenol, the Sex Pheromone of the Green Flagellate Chlamydomonas." Liebigs Annalen/Recueil. 825-838 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Shin-ichi Takanashi and Kenji Mori, Pheromone Synthesis, CLXXXV.: "Synthesis of the Analogues of Lurlenic Acid with a Modified Sugar Part : Chlamydomonas Responds Only to the D-Xyloside" Liebigs Annalen/Recueil. 1081-1084 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Shin-ichi Takanashi and Kenji Mori, Pheromone Synthesis, CLXXXVII.: "Synthesis of the Analogues of Lurlenic Acid with Modification in the Side-Chain or in the Aromatic Nucleus : Summary of the Structure-ACtivity Relationships." Eur.J.Org.Chem.43-55 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Hirosato Takikawa, Ken-ichiro Shimbo and Kenji Mori, Pheromone Synthesis, CLXXXIII.: "Synthesis of (1R,2R,5S,7R)-and (1R,2S,5S,7R)-2-Hydroxy-exo-brevicomin, the Components of the Male-Produced Volatile of the Mountain Pine Beetle, Dendroctonus ponderosae." Liebigs Annalen/Recueil. 821-824 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yusuke Yokoyama and Kenji Mori, Pheromone Synthesis, CLXXXII.: "Synthesis of (1R,! 'R,5'R,7'R)-and (1S,1'R,5'R,7'R)-1-Hydroxy-exo-brevicomin, the Components of the Male-Produced Volatile of the Mountain Pine Beetle, Dendroctonus ponderosae." Leibigs Annalen/Recueil. 845-849 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Hirosato Takikawa, Satoshi Sano and Kenji Mori, Pheromone Synthesis, CLXXXVI.: "Synthesis of (1S,2R,5R)-Bicolorin, the Aggregation Pheromone of Male Beech Bark Beetle (Taphrorychus bicolor), and Its (1R,2R,5S)-Isomer." Liebigs Annalen/Recueil. 2495-2498 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yutaka Nishimura and Kenji Mori, Pheromone Synthesis, CLXXXVIII.: "A New Synthesis of (-)-Frontalin, the Bark Beetle Pheromone." Eur.J.Org.Chem.233-236 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kenji Mori, Satoshi Sano Yusuke Yokoyama, Masahiko Bando, Masaru Kido, Pheromone Synthesis, CXC.: "Synthesis of Stegobiol and Its Oxidation to Stegobinone, the Components of the Female-produced Sex Pheromone of the Drugstore Beetle." Eur.J.Org.Chem.1135-1141 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kenji Mori, Motonobu Takenaka, Pheromone Synthesis, CXCI.: "Sythesis of the Enantiomers of 8-Hydroxy-2,5,8-trimethyl-4-nonanone, the Myxobacterial Pheromone of Stegmatella aurantiaca to Induce the Formation of Its Fruiting Body." Eur.J.Org.Chem.2181-2184 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kenji Domon, Kenji Mori, Pheromone Synthesis, CXCIII.: "Simple Synthesis of *-Stigmolone (8-Hydroxy-2,5,8-trimethyl-4-nonanone), the Pheromone of Stegmatella auratiaca." Eur.J.Org.Chem.(in the press). (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] J.G.C.Hamilton, A.M.Hooper, K.Mori, J.A.Pickett, S.Sano: "3-Methyl-alpha-himachalene confirmed, and the relative stereochemistry defined, by synthesis as the sex pheromone of the sandfly Lutxomyia longipalpis from Jacobina, Brazil." Chemical Communications. (in the press). (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Satoshi Sano, Kenji Mori, Pheromone Synthesis, CXCV.: "Synthesis of (1R^*,3R^*,7R^*)-3-Methyl-alpha-himachalene, the Racemate of the Male-produced Sex Pheromone of the Sandfly Lutzomyia longipalpis from Jacobina, Brazil." Eur.J.Org.Chem.(in the press). (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Shin-etsu Muto, Yutaka Nishimura, Kenji Mori, Pheromone Synthesis, CXCVI.: "Synthesis of Germacrene-B and Its Extention to the Synthesis of *-90Methylgermacrene-B,the Racemate of the Male-produced Sex Pheromone of the Sandfly Lutzomyia longipalpis from Lapinha, Brazil." Eur.J.Org.Chem.(in the press). (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Takuya Tashiro, Kenji Mori, Pheromone Synthesis, CXCVII.: "Synthesis of the Enantiomers of 2-sec-Butyl-4,5-dihydrothiazole and (1R,5S,7R)-3,4-Dehydro-exo-brevicomin, the Pheromone Components of the Male Mouse, Mus musculus" Eur.J.Org.Chem.(in the press). (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kenji Mori: "Pheromones Synthesis and Bioactivity." Chemical Communications. 1153-1158 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kenji Mori: "Chirality and Insect Pheromones" Chirality. 578-586 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kenji Mori: "Semicochemicals-Synthesis, Stereochemistry and Bioactivity" Eur.J.Org.Chem.1479-1489 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kenji Mori: "Chapter 8 : Separation of Enantiomers and Determination of Absolute Configuration" J.G.Millar, K.F.Haynes, Eds.Methods in Chemical Ecology, Vol.1,390 pp., Kluwer Academic Publishers.295-338 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kenji Mori: "Chapter 6 : Chirality in Insect Juvenile Hormones and Pheromones" N.Kurihara, J.Miyamoto.Eds., Chirality in Agrochemicals, 269 pp., John Wiley & Sons. 199-257 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kenji Mori: "Chapter 1 ; Overview" Kenji Mori, Ed.Comprehensive Natural Products Chemistry, Vol.8,749pp., Elsevier Science Ltd.1-18 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kenji MORI: "Chirality and Insect Pheromones" Chirality. 10・7. 578-586 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Kenji MORI: "Semiochemicals-Synthesis, Stereochemistry and Bioactivity" European Journal of Organic Chemistry. No.8. 1479-1489 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] S.Takanashi,K.Mori: "Synthesis of the Analogues of Lurlenic Acid with Modification in the Side-Chain or in the Aromatic Nucleus:Summary of the Structure-Activity Relationships" European Journal of Organic Chemistry. No.1. 43-55 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Y.Nishimura,K.Mori: "A New Synthesis of (-)-Frontalin, the Bark Beetle Pheromone" European Journal of Organic Chemistry. 233-236 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] K.Mori,S.Sano,Y.Yokoyama,M.Bando,M.Kido: "Synthesis of Stegobiol and Its Oxidation to Stegobinone the Components of the Female-producead Sex Pheromone of the Dugstore" European Journal of Organic Chemistry. 1135-1148 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] K.Mori,M.Takenaka: "Synthesis of the Enantiomers of 8-Hydroxy-2.5,8-trimethyl-4-nonano the Myxobacterial Pheromone of Stigmatella aurantiaca" European Journal of Organic Chemistry. 2181-2184 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] K.Domon,K.Mori: "Simple Synthesis of (±)-Stigmolone (8-Hydroxy-2.5,8-Trimethyl-4-nonanone), the Pheromone of Stigmatella aurantiaca" European Journal of Organic Chemistry. 印刷中. (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] J.G.C.Hamilton,A.M.Hooper,K.Mori,J.A.Pickett,S.Sano: "3-methyl-α-himachalene Confirmed and the relative stereochemisty defined by synthesis as the sex pheromone of the sandfly" Chemical Communications. 印刷中. (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] S.Sano,K.Mori: "Synthesis of (1R^*,3R^*,7R^*)-3-Methyl-α-himachalene, the Racemate of the Male-produced Sex Pheromone of the Sandfly" European Journal of Organic Chemistry. 印刷中. (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] S.Muto,Y.Nishimura,K.Mori: "Synthesis of Germacrene-B and Its Extension to the Synthesis of (±)-9-Methylgermacrene-B, the Racemate of the Male-produced Sex Pheromone of the Sandfly" European Journal of Organic Chemistry. 印刷中. (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] T.Tashiro,K.Mori: "Synthesis of the Enantiomers of 2-sec-Butyl-4,5-dihydrothiazok and (1R,5S,7R)-3,4-Dehydro-exo-brevicomin, the Pheromone" European Journal of Organic Chemistry. 印刷中. (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Kenji MORI (J.G.Millar,K.F.Haynes編): "Methods in Chemical Ecology Volume 1. Chapter 8:Separation of Enantiomers and Determination of Absolute Configuration" Kluwer Academic Publishers, 390(295-338) (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Kenzi Mori (N.Kurihara, J.Miyamoto編): "Chirality in Agrochemicals Chapter 6:Chirality in Insect Juvenile Hormones and Pheromones" John Wiley & Sons, 269(199-257) (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Kenji MORI (Kenji MORI編): "Comprehensive Natural Products Chemistry Vol8. Chapter1:Overview" Elsevcer Science Ltd., 749(1-18) (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Kenji Mori: "Pheromones : Synthesis and Bioactivity" Chemical Communications. 1153-1158 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] S.Takanashi, K.Mori: "Synthesis of Lurlenic Acid and Lurlenol,the sex pheromone of the Green Flagellate Chlamyolomonas" Liebigs Annalen. 825-838 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] S.Takanashi, K.Mori: "Synthesis of the Analogues of Lurlenic Acid with a Modified Suger Part : Chlamydomonas responds only to the D-xyloside" Liebigs Annalen. 1081-1084 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] K.Mori, H.Takikawa, Y.Nishimura, H.Horikiri: "Synthesis of (-) -exo- Isobrericomin and its (-) -endo-Isomer" Liebigs Annalen. 327-332 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Y.Yokoyama, K.Mori: "Synthesis of (1R,1′R,5′R,7′R)-and (1S,1′R,5′R,7′R) -Hydroxy-exo- brevicomin" Liebigs Annalen. 845-849 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] H.Takikawa, S.Sano, K.Mori: "Synthesis of (1S,2R,5R) -Bicolorin" Liebigs Annalen. 2495-2498 (1997)

    • Related Report
      1997 Annual Research Report

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Published: 1997-04-01   Modified: 2016-04-21  

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