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2006 Fiscal Year Final Research Report Summary

Synthetic Studies on Semiochemicals for the Control of Agricultural Pests

Research Project

Project/Area Number 16380075
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionTohoku University

Principal Investigator

KUWAHARA Shigefumi  Tohoku University, Graduate School of Agricultural Science, Division of Life Science, Professor, 大学院農学研究科, 教授 (30170145)

Co-Investigator(Kenkyū-buntansha) KIYOTA Hiromasa  Tohoku University, Graduate School of Agricultural Science, Division of Life Science, Associate Professor, 大学院農学研究科, 助教授 (30234397)
Project Period (FY) 2004 – 2006
Keywordsenokipodin / pteridic acid / tabtoxinine / litseaverticillol / Drosophila / communiol / pyricuol / epoxyquinol
Research Abstract

The total synthesis of the following biologically active natural products have been accomplished : (1)enokipodins A,B,C, and D (highly oxygenated a-cuparenone-type sesquiterpenoids exhibiting antimicrobial activity produced by the edible mushroom, Flammulina velutipes) ; (2)pteridic acids A and B (potent plant-growth promoters possessing unique spirocyclic polyketidic structures isolated form the phytoepiphytic actinomycete, Streptomyces hygroscopicus TP-A0451) ; (3)tabtoxinine-β-lactom (a phytotoxin produced by the pathogen Pseudomonas syringae pv. tabaci) ; (4)pteroenone (a defensive metabolite of the pteropod, Clione antarctica) ; (5)the major sex pheromone components of the fruit flies, Drosophila ananassae and D.pallidosa ; (6)communiols A,B,C,D,E,F,and H (antimicrobial metabolites produced by the coprophilous fungus, Podospora communis) ; (7)pyricuol (a phytotoxin produced by the rice blast fungus, Magnaporthe grisea) ; (8)gizzerosine (a potent inducer of gizzard erosion in chicks contained in heat-treated fish meal) ; (9)apoptosis-inducing polyunsaturated conjugated fatty acids ; (10)litseaverticillols A and B (anti-HIV sesquterpenoids bearing a novel carbon sketeton produced by the perennial shrub, Litsea verticillata). Partial syntheses of pamamycin-635A (an arerial mycelium-inducing metabolite produced by Streptomyces alboniger) and elaiophylin (an antibiotic as well as a plant-growth inhibitor) were conducted. Studies directed toward the total synthesis of azadirachtin (a potent antifeedant contained in the neem tree, Azadirachta indica) was also made.

  • Research Products

    (38 results)

All 2007 2006 2005 2004

All Journal Article (38 results)

  • [Journal Article] Cross-metathesis approach to a (2E,4E)-dienoic acid intermediate for the synthesis of elaiolide2007

    • Author(s)
      Akira Morita, Shigefumi Kuwahara
    • Journal Title

      Tetrahedron Lett. 482

      Pages: 3163-3166

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Cross-metathesis approach to a (2E,4E)-dienoic acid intermediate for the synthesis of elaiolide.2007

    • Author(s)
      Akira Morita, Shigefumi Kuwahara
    • Journal Title

      Tetrahedron Lett. 48 (18)

      Pages: 3163-3166

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Stereochemical revision for communiols D and H through synthesis2006

    • Author(s)
      Masaru Enomoto, Takashi Nakahata, Shigefumi Kuwahara
    • Journal Title

      Tetrahedron 62

      Pages: 1102-1109

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Enantioselective total synthesis of litseaverticillols A and B2006

    • Author(s)
      Akira Morita, Shigefumi Kuwahara
    • Journal Title

      Org. Lett. 8

      Pages: 1613-1616

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Total synthesis of pteridic acids A and B2006

    • Author(s)
      Takashi Nakahata, Shohei Fujimura, Shigefumi Kuwahara
    • Journal Title

      Chem. Eur. J. 12

      Pages: 4581-4593

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Enantioselective total synthesis and stereochemical revision of communiols E and F2006

    • Author(s)
      Masaru Enomoto, Shigefumi Kuwahara
    • Journal Title

      J. Org. Chem. 71

      Pages: 6287-6290

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Synthesis of (S)-gizzerosine, a potent inducer of gizzard erosion in chicks2006

    • Author(s)
      Yasuharu Shimasaki, Hiromasa Kiyota, Minoru Sato, Shigefumi Kuwahara
    • Journal Title

      Tetrahedron 62

      Pages: 9628-9634

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Enantioselective Synthesis of the (1S,5R)-Enantiomer of Litseaverticillols A and B2006

    • Author(s)
      Akira Morita, Hiromasa Kiyota, Shigefumi Kuwahara
    • Journal Title

      Biosci. Biotechnol. Bichem. 70

      Pages: 2564-2566

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Stereochemical revision for communiols D and H through synthesis.2006

    • Author(s)
      Masaru Enomoto, Takashi Nakahata, Shigefumi Kuwahara
    • Journal Title

      Tetrahedron 62 (6)

      Pages: 1102-1109

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Enantioselective total synthesis of litseaverticillols A and B.2006

    • Author(s)
      Akira Morita, Shigefumi Kuwahara
    • Journal Title

      Org.Lett. 8 (8)

      Pages: 1613-1616

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Total synthesis of pteridic acids A and B.2006

    • Author(s)
      Takashi Nakahata, Shohei Fujimura, Shigefumi Kuwahara
    • Journal Title

      Chem.Eur.J. 12 (17)

      Pages: 4581-4593

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Enantioselective total synthesis and stereochemical revision of communiols E and F.2006

    • Author(s)
      Masaru Enomoto, Shigefumi Kuwahara
    • Journal Title

      J.Org.Chem. 71 (16)

      Pages: 6287-6290

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Synthesis of (S)-gizzerosine, a potent inducer of gizzard erosion in chicks.2006

    • Author(s)
      Yasuharu Shimasaki, Hiromasa Kiyota, Minoru Sato, Shigefumi Kuwahara
    • Journal Title

      Tetrahedron 62 (41)

      Pages: 9628-9634

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Enantioselective Synthesis of the (IS,5R)-Enantiomer of Litseaverticillols A and B.2006

    • Author(s)
      Akira Morita, Hiromasa Kiyota, Shigefumi Kuwahara
    • Journal Title

      Biosci.Biotechnol.Bichem. 70 (10)

      Pages: 2564-2566

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Enantioselective total synthesis of enokipodins A-D, antimicrobial sesquiterpenes produced by the mushroom, Flammulina velutipes2005

    • Author(s)
      Mana Saito, Shigefumi Kuwahara
    • Journal Title

      Biosci. Biotechnol. Biochem. 69

      Pages: 374-381

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Enantioselective total synthesis of pteridic acid A2005

    • Author(s)
      Takashi Nakahata, Shigefumi Kuwahara
    • Journal Title

      Chem. Commun. (8)

      Pages: 1028-1030

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Enantioselective total synthesis of antiangeogenic pentaketide dimmers, epoxyquinols A and B, through an asymmetric aldol approach to their common monomeric precursor2005

    • Author(s)
      Shigefumi Kuwahara, Sunao Imada
    • Journal Title

      Tetrahedron Lett. 46

      Pages: 547-549

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Synthesis of the conjugated trienes 5E,7E,9E,14Z,17Z-eicosapentaenoic acid and 5Z,7E,9E,14Z,17Z-eicosapentaenoic acid, and their induction of apoptosis in cultured human tumor cells2005

    • Author(s)
      Tsuyoshi Tsuzuki, Kazumi Tanaka, Shigefumi Kuwahara, Teruo Miyazawa
    • Journal Title

      Lipids 40

      Pages: 147-154

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Synthesis of southern (C1'-C11') fragment of pamamycin-635A2005

    • Author(s)
      Ayako Miura, Hiromasa Kiyota, Shigefumi Kuwahara
    • Journal Title

      Tetrahedron 61

      Pages: 1061-1067

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] First synthesis of (+)-pteroenone : a defensive metabolite of the abducted antarctic pteropod Clione antarctica2005

    • Author(s)
      Yoko Nakamura, Hiromasa Kiyota, Bill J. Baker, Shigefumi Kuwahara
    • Journal Title

      Synlett (4)

      Pages: 635-636

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Simple Synthesis of the Major Sex Pheromone Components of Drosophila ananassae and D. pallidos2005

    • Author(s)
      Akira Morita, Shigeru Matsuyma, Yuzuru Oguma, Shigefumi Kuwahara
    • Journal Title

      Biosci. Biotechnol. Biochem. 69

      Pages: 1620-1623

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Enantioselective synthesis and stereochemical revision of communiols A-C2005

    • Author(s)
      Shigefumi Kuwahara, Masaru Enomoto
    • Journal Title

      Tetrahedron Lett. 46

      Pages: 6297-6300

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Synthesis to determine the absolute configuration of (-)-pyricuol, a phytotoxin isolated from rice blast disease fungus Magnaporthe grisea2005

    • Author(s)
      Yoko Nakamura, Hiromasa Kiyota, Rumi Ueda, Shigefumi Kuwahara
    • Journal Title

      Tetrahedron Lett. 46

      Pages: 7107-7109

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Facile synthesis of (S)-gizzerosine - A potent inducer of gizzard erosion in chicks -using successive zinc-mediated and palladium -catalyzed coupling reactions2005

    • Author(s)
      Yasuharu Shimazaki, Hiromasa Kiyota, Minoru Sato, Shigefumi Kuwahara
    • Journal Title

      Synthesis (19)

      Pages: 3191-3192

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Enantioselective total synthesis of enokipodins A-D, antimicrobial sesquiterpenes produced by the mushroom, Flammulina velutipes.2005

    • Author(s)
      Mana Saito, Shigefumi Kuwahara
    • Journal Title

      Biosci.Biotechnol.Biochem. 69 (2)

      Pages: 374-381

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Enantioselective total synthesis of pteridic acid A.2005

    • Author(s)
      Takashi Nakahata, Shigefumi Kuwahara
    • Journal Title

      Chem.Commun. (8)

      Pages: 1028-1030

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Enantioselective total synthesis of antiangeogenic pentaketide dimmers, epoxyquinols A and B, through an asymmetric aldol approach to their common monomeric precursor.2005

    • Author(s)
      Shigefumi Kuwahara, Sunao Imada
    • Journal Title

      Tetrahedron Lett. 46 (4)

      Pages: 547-549

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Synthesis of the conjugated trienes 5E,7E,9E,14Z,17Z-eicosapentaenoic acid and 5Z,7E,9E,14Z,17Z-eicosapentaenoic acid, and their induction of apoptosis in cultured human tumor cells.2005

    • Author(s)
      Tsuyoshi Tsuzuki, Kazumi Tanaka, Shigefumi Kuwahara, Teruo Miyazawa
    • Journal Title

      Lipids 40 (2)

      Pages: 147-154

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Synthesis of southern (C1'-C11') fragment of pamamycin-635A.2005

    • Author(s)
      Ayako Miura, Hiromasa Kiyota, Shigefumi Kuwahara
    • Journal Title

      Tetrahedron 61 (5)

      Pages: 1061-1067

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] First synthesis of (+)-pteroenone : a defensive metabolite of the abducted antarctic pteropod Clione antarctica.2005

    • Author(s)
      Yoko Nakamura, Hiromasa Kiyota, Bill J.Baker, Shigefumi Kuwahara
    • Journal Title

      Synlett (4)

      Pages: 635-636

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Simple Synthesis of the Major Sex Pheromone Components of Drosophila ananassae and D.pallidosa.2005

    • Author(s)
      Akira Morita, Shigeru Matsuyma, Yuzuru Oguma, Shigefumi Kuwahara
    • Journal Title

      Biosci.Biotechnol.Biochem. 69 (8)

      Pages: 1620-1623

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Enantioselective synthesis and stereochemical revision of communiols A-C.2005

    • Author(s)
      Shigefumi Kuwahara, Masaru Enomoto
    • Journal Title

      Tetrahedron Lett. 46 (37)

      Pages: 6297-6300

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Synthesis to determine the absolute configuration of (-)pyricuol, a phytotoxin isolated from rice blast disease fungus Magnaporthe grisea.2005

    • Author(s)
      Yoko Nakamura, Hiromasa Kiyota, Rumi Ueda, Shigefumi Kuwahara
    • Journal Title

      Tetrahedron Lett. 46 (42)

      Pages: 7107-7109

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Facile synthesis of (S)-gizzerosine -A potent inducer of gizzard erosion in chicks-using successive zinc-mediated and palladium-catalyzed coupling reactions.2005

    • Author(s)
      Yasuharu Shimazaki, Hiromasa Kiyota, Minoru Sato, Shigefumi Kuwahara
    • Journal Title

      Synthesis (19)

      Pages: 3191-3192

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Enantioselective total synthesis of enokipodins A-D2004

    • Author(s)
      Shigefumi Kuwaharad, Mana Saito
    • Journal Title

      Tetrahedron Lett. 45

      Pages: 5047-5049

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Facile synthesis of (-)-tabtoxinine-β-lactam and its (3'R)-isomer2004

    • Author(s)
      Hiromasa Kiyota, Takafumi Takai, Masatoshi Saito, Osamu Nakayama, Takayuki Oritani, Shigefumi Kuwahara
    • Journal Title

      Tetrahedron Lett. 45

      Pages: 8191-8194

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Enantioselective total synthesis of enokipodins A-D.2004

    • Author(s)
      Shigefumi Kuwahara, Mana Saito
    • Journal Title

      Tetrahedron Lett. 45 (26)

      Pages: 5047-5049

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Facile synthesis of (-)-tabtoxinine-β-lactam and its (3'R)-isomer.2004

    • Author(s)
      Hiromasa Kiyota, Takafumi Takai, Masatoshi Saito, Osamu Nakayama, Takayuki Oritani, Shigefumi Kuwahara
    • Journal Title

      Tetrahedron Lett. 45 (44)

      Pages: 8191-8194

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

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Published: 2008-05-27  

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