Synthetic Studies on Complex Terpenoids with Bioactivities as Lead Compounds of Agricultural Chemicals

• Project/Area Number: 21350021
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Hokkaido University
• Principal Investigator: TANINO Keiji 北海道大学, 大学院・理学研究院, 教授 (40217146)
• Project Period (FY): 2009 – 2011
• Project Status: Completed (Fiscal Year 2011)
• Budget Amount: ¥19,370,000 (Direct Cost: ¥14,900,000、Indirect Cost: ¥4,470,000); Fiscal Year 2011: ¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000); Fiscal Year 2010: ¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000); Fiscal Year 2009: ¥8,190,000 (Direct Cost: ¥6,300,000、Indirect Cost: ¥1,890,000)
• Keywords: 合成有機化学 / 有機化学 / 天然物化学 / 全合成 / 農薬

Research Abstract

Potato cyst nematode is a troublesome parasite that live on, and destroy, important vegetable plants including potatoes. We have achieved the first total synthesis of solanoeclepin A, the key hatch-stimulating substance for potato cyst nematode, through 52-step transformations. The synthetic solanoeclepin A was shown to stimulate the hatching activity at high dilution in water, and the present synthesis has the potential to contribute to the critical food supply issue.

Research Products

• [Journal Article] ジャガイモシストセンチュウふ化促進物質の化学合成.-環境調和型シストセンチュウ駆除剤への期待- (2012)
  • Author(s): 谷野圭持
  • Journal Title: 農林水産技術研究ジャーナル Volume: 35,(5) Pages: 45-48
  • NAID: 10030138638
  • URL: http://www.afftis.or.jp/books/order/journal/yousi/3505.htm
• [Journal Article] Total Synthesis of Solanoeclepin A (2011)
  • Author(s): K. Tanino, M. Takahashi, Y. Tomata, H. Tokura, T. Uehara, T. Narabu, and M. Miyashita
  • Journal Title: Nature Chem Volume: 3, (6) Issue: 6 Pages: 484-488
  • DOI: 10.1038/nchem.1044
  • Peer Reviewed
• [Journal Article] Formal [6+4] Cycloaddition of a Dicobalt Acetylene Complex with Furan Derivatives (2011)
  • Author(s): K. Dota, T. Shimizu, S. Hasegawa, M. Miyashita, and K. Tanino
  • Journal Title: Tetrahedron Lett Volume: 52, (8) Issue: 8 Pages: 910-912
  • DOI: 10.1016/j.tetlet.2010.12.063
  • Peer Reviewed
• [Journal Article] Synthetic Studies of the Zoanthamine Alkaloids : Total Synthesis of Zoanthenol Based on Isoaromatization Strategy (2011)
  • Author(s): 谷野圭持、宮下正昭, ほか2名
  • Journal Title: Chemistry an Asian Journal Volume: 6 Issue: 3 Pages: 922-931
  • DOI: 10.1002/asia.201000552
  • Peer Reviewed
• [Journal Article] Direct Synthesis of Fluorescent 1,3a,6a-Triazapentalene Derivatives via Click-Cyclization- Aromatization Cascade Reaction (2011)
  • Author(s): K. Namba, A. Osawa, S. Ishizaka, N. Kitamura, and K. Tanino
  • Journal Title: J. Am. Chem. Soc Volume: 133, (8) Issue: 30 Pages: 11466-11469
  • DOI: 10.1021/ja203917r
  • Peer Reviewed
• [Journal Article] Asymmetric Total Synthesis of Glycinoeclepin A: Generation of a Novel Bridgehead Anion Species (2010)
  • Author(s): Y. Shiina, Y. Tomata, M. Miyashita, and K. Tanino
  • Journal Title: Chemistry Letters Volume: 39 Issue: 8 Pages: 835-837
  • DOI: 10.1246/cl.2010.835
  • NAID: 130004425946
  • ISSN: 0366-7022, 1348-0715
  • Peer Reviewed
• [Journal Article] Synthetic Studies on Azadirachtin : Stereoselective Construction of the ABCE Ring System (2010)
  • Author(s): D. Nakagawa, M. Miyashita, and K. Tanino
  • Journal Title: Tetrahedron Lett Volume: 51,(20) Issue: 20 Pages: 2771-2773
  • DOI: 10.1016/j.tetlet.2010.03.077
  • Peer Reviewed
• [Journal Article] Asymmetric Total Synthesis of Glycinoeclepin A : Generation of a Novel Bridgehead Anion Species (2010)
  • Author(s): 宮下正昭、谷野圭持, ほか2名
  • Journal Title: Chemistry Letters Volume: Vol.39 Pages: 835-837
  • NAID: 10027183714
  • Peer Reviewed
• [Journal Article] Practical Synthesis of (K)- and (Z)-2-Silyl-3-penten-l-ols with High Enantiopurity (2010)
  • Author(s): 福田耕一朗、宮下正昭、谷野圭持
  • Journal Title: Tetrahedron Letters Volume: Vol.51 Pages: 4523-4525
  • Peer Reviewed
• [Journal Article] Synthetic Studies on Azadirachtin : Stereoselective Construction of the ABCE Ring System (2010)
  • Author(s): 中川大輔、宮下正昭、谷野圭持
  • Journal Title: Tetrahedron Letters Vol.51(印刷中)
  • Peer Reviewed
• [Presentation] Asymmetric Total Synthesis of Solanoeclepin A (2012)
  • Author(s): 谷野圭持
  • Organizer: The 5th GCOE International Symposium : Catalysis as the Basis for the Innovation in Materials Science
  • Place of Presentation: 北海道大学(札幌市)(招待講演)
  • Year and Date: 2012-02-21
• [Presentation] Design, Tactics, and Findings in NaturalProduct Synthesis (2011)
  • Author(s): K. Tanino
  • Organizer: The Nagoya Medal of Organic Chemistry 2011
  • Place of Presentation: Nagoya
  • Year and Date: 2011-11-14
• [Presentation] Design, Tactics, and Findings in Natural Product Synthesis (2011)
  • Author(s): 谷野圭持
  • Organizer: The Nagoya Medal of Organic Chemistry 2011
  • Place of Presentation: 名古屋大学(名古屋市)(招待講演)
  • Year and Date: 2011-11-14
• [Presentation] Total Synthesis of Solanoeclepin A (2011)
  • Author(s): K. Tanino
  • Organizer: 22nd French-Japanese Symposium of Medicinal and Fine Chemistry
  • Place of Presentation: Rouen
  • Year and Date: 2011-09-14
• [Presentation] Total Synthesis of Solanoeclepin A (2011)
  • Author(s): 谷野圭持
  • Organizer: 22nd French-Japanese Symposium of Medicinal and Fine Chemistry
  • Place of Presentation: the Chambre de Commerce et d-Industrie(フランス)(招待講演)
  • Year and Date: 2011-09-14
• [Presentation] シストセンチュウ孵化促進物質の不斉全合成 (2011)
  • Author(s): 谷野圭持
  • Organizer: 第28回有機合成化学セミナー
  • Place of Presentation: 天童
  • Year and Date: 2011-09-02
• [Presentation] シストセンチュウ孵化促進物質の不斉全合成 (2011)
  • Author(s): 谷野圭持
  • Organizer: 第28回有機合成化学セミナー
  • Place of Presentation: ホテル滝の湯(天童市)(招待講演)
  • Year and Date: 2011-09-02
• [Presentation] Asymmetric Total Synthesis of Solanoeclepin A (2011)
  • Author(s): K. Tanino
  • Organizer: NTU-JSPS Joint Symposium Recent Advances in Organic Syntheses
  • Place of Presentation: Singapore
  • Year and Date: 2011-08-01
• [Presentation] Asymmetric Total Synthesis of Solanoeclepin A (2011)
  • Author(s): 谷野圭持
  • Organizer: NTU-JSPS Joint Symposium "Recent Advances in Organic Syntheses"
  • Place of Presentation: 南洋理工大学(シンガポール)(招待講演)
  • Year and Date: 2011-08-01
• [Presentation] シスト線虫孵化促進物質ソラノエクレピンAおよびグリシノエクレピンAの不斉全合成 (2010)
  • Author(s): 谷野圭持
  • Organizer: 第22回名古屋コンファレンス「グリーン&ライフ分子創製化学の最先端」
  • Place of Presentation: 名古屋大学シンポジオン(名古屋市) 招待講演
  • Year and Date: 2010-11-26
• [Presentation] Asymmetric Total Synthesis of Glycinoeclepin A (2010)
  • Author(s): 谷野圭持
  • Organizer: The Pre-Symposium of 5th International Conference on Cutting-Edge Organic Chemistry in Asia
  • Place of Presentation: 高雄(台湾) 招待講演
  • Year and Date: 2010-11-06
• [Presentation] Total Synthesis of Polycyclic Natural Products Having Quaternary Stereogenic Carbon Atoms (2009)
  • Author(s): 谷野圭持
  • Organizer: The Fifth Sino-Japanese Symposium on Organic Chemistry for Young Scientists
  • Place of Presentation: 成都(中国)
  • Year and Date: 2009-10-09
• [Remarks]
  • URL: http://barato.sci.hokudai.ac.jp/~oc2/