Synthetic study on bioactive natural product, causing hatching phenomenon toward potato Cyst nematodes, by construction of highly-substituted cyclobutane skeleton

2011 Fiscal Year Final Research Report

• Project/Area Number: 22780102
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Bioproduction chemistry/Bioorganic chemistry
• Research Institution: Nagoya University
• Principal Investigator: ADACHI Masaatsu 名古屋大学, 生命農学研究科, 助教 (80432251)
• Project Period (FY): 2010 – 2011
• Keywords: 天然物化学 / 有機化学 / 合成化学

Research Abstract

Synthesis of solanoeclepin A, the most active hatching agent of potato cyst nematode isolated from hydroponic potato cultures was examined not only for the chemical supply of solanoeclepin A but also for the structure-activity relationship study. As a result, the new ring expansion reaction was discovered for the synthesis of a chiral hexahydroazulene skeleton possessing an angular methyl group. Furthermore, synthesis of oxabicylo skeleton, corresponding to the left-hand nucleus, was also achieved.

Research Products

• [Journal Article] A Concise Synthesis of a Highly Strained Cyclobutane in Solanoeclepin A by Radical Cyclization (2012)
  • Author(s): Komada, T.; Adachi, M.; Nishikawa, T
  • Journal Title: Chem. Lett Volume: 41 Pages: 287-289
  • DOI: DOI:10.1246/cl.2012.287
  • Peer Reviewed
• [Journal Article] Stereocontrolled Synthesis of an Indole Moiety of Sespendole and Stereochemical Assignment of the Side Chain (2012)
  • Author(s): Adachi, M.; Higuchi, K.; Thasana, N.; Yamada, H.; Nishikawa, T.
  • Journal Title: Org. Lett Volume: 14 Pages: 114-117
  • DOI: DOI:10.1021/ol202895u
  • Peer Reviewed
• [Journal Article] Total Synthesis of Polygalolide A (2011)
  • Author(s): Adachi, M.; Yamada, H.; Isobe, M.; Nishikawa, T
  • Journal Title: Org. Lett Volume: 13 Pages: 6532-6535
  • DOI: DOI:10.1021/ol2028256
  • Peer Reviewed
• [Journal Article] A New Ring Expansion for a Chiral Hexahydroazulene Skeleton Possessing an Angular Methyl Group (2011)
  • Author(s): Adachi, M.; Komada, T.; Nishikawa, T
  • Journal Title: Org. Chem Volume: 76 Pages: 6942-6945
  • DOI: DOI:10.1021/jo201153h
  • Peer Reviewed
• [Journal Article] Synthesis of an Advanced Intermediate Bearing Two Hydroxy Groups for(-)-Tetrodotoxin and Its Analogs (2010)
  • Author(s): Nishikawa, T.; Koide, Y.; Adachi, M.; Isobe, M
  • Journal Title: Bull. Chem. Soc Volume: 83 Pages: 66-68
  • DOI: DOI:10.1246/bcsj.20090223
  • Peer Reviewed
• [Presentation] インドールアルカロイドSespendole芳香環部分の合成研究と立体化学の決定 (2012)
  • Author(s): 樋口恵子、安立昌篤、Nopporn Thasana、西川俊夫
  • Organizer: 日本農芸化学会2012年度大会
  • Place of Presentation: 京都
  • Year and Date: 20120322-26
• [Presentation] 8-デオキシテトロドトキシンの立体制御合成 (2012)
  • Author(s): 所聖太、安立昌篤、磯部稔、西川俊夫
  • Organizer: 日本農芸化学会2012年度大会
  • Place of Presentation: 京都
  • Year and Date: 20120322-26
• [Presentation] テトロドトキシンおよびチリキトキシンの合成研究 (2012)
  • Author(s): 榊原良、安立昌篤、西川俊夫
  • Organizer: 日本農芸化学会2012年度大会
  • Place of Presentation: 京都
  • Year and Date: 20120322-26
• [Presentation] 植物毒素Tagetitoxinの合成研究 (2012)
  • Author(s): 山田ひと美、安立昌篤、西川俊夫
  • Organizer: 日本農芸化学会2012年度大会
  • Place of Presentation: 京都
  • Year and Date: 20120322-26
• [Presentation] ソラノエクレピンA右側部分の合成研究 (2012)
  • Author(s): 駒田武馬、安立昌篤、西川俊夫
  • Organizer: 日本農芸化学会2012年度大会
  • Place of Presentation: 京都
  • Year and Date: 20120322-26
• [Presentation] Total Synthesis of Polygalolide A, Isolated from a Medicinal Plant (2012)
  • Author(s): Masaatsu Adachi
  • Organizer: The 1st Nagoya Symposium on Green Synthesis & Catalysis
  • Place of Presentation: Nagoya, Japan
  • Year and Date: 2012-03-13
• [Presentation] Total Synthesis of Polygalolide A (2011)
  • Author(s): Masaatsu Adachi, Hitomi Yamada, Minoru Isobe, Toshio Nishikawa
  • Organizer: The 6th International Conference on Cutting-edge Organic Chemistry in Asia(ICCEOCA-6), The 2nd New phase International Conference on Cutting-edge Organic Chemistry in Asia
  • Place of Presentation: Hong Kong, P. R. China
  • Year and Date: 20111211-15
• [Presentation] テトロドトキシンおよびチリキトキシンの合成研究 (2011)
  • Author(s): 榊原良、安立昌篤、佐竹佳樹、磯部稔、西川俊夫
  • Organizer: 第100回有機合成シンポジウム
  • Place of Presentation: 東京
  • Year and Date: 20111110-11
• [Presentation] インドールアルカロイドSespendole芳香族部分の合成研究 (2011)
  • Author(s): 樋口恵子、Nopporn Thasana、杉野公美、安立昌篤、中崎敦夫、西川俊夫
  • Organizer: 第42回中部化学関係学協会支部連合秋季大会
  • Place of Presentation: 長野
  • Year and Date: 20111105-06
• [Presentation] 8-デオキシテトロドトキシンの立体制御合成 (2011)
  • Author(s): 所聖太、安立昌篤、磯部稔、西川俊夫
  • Organizer: 第42回中部化学関係学協会支部連合秋季大会
  • Place of Presentation: 長野
  • Year and Date: 20111105-06
• [Presentation] Total Synthesis of Polygalolide A (2011)
  • Author(s): 山田ひと美、安立昌篤、磯部稔、西川俊夫
  • Organizer: 第5回リトリートKeep Our Scientific Interaction Alive～科学で交流し続けよう～
  • Place of Presentation: 長浜
  • Year and Date: 20110905-06
• [Presentation] Total Synthesis of 5, 6, 11-Trideoxytetrodotoxin (2011)
  • Author(s): 安立昌篤、榊原良、佐竹佳樹、磯部稔、西川俊夫
  • Organizer: 第5回リトリートKeep Our Scientific Interaction Alive～科学で交流し続けよう～
  • Place of Presentation: 長浜
  • Year and Date: 20110905-06
• [Presentation] 8-デオキシテトロドトキシンの合成研究 (2011)
  • Author(s): 所聖太、安立昌篤、磯部稔、西川俊夫
  • Organizer: 第46回天然化学談話会
  • Place of Presentation: 熱川
  • Year and Date: 20110707-09
• [Presentation] 分子内C.グリコシル化反応を利用したポリガロリドAの全合成 (2011)
  • Author(s): 山田ひと美、安立昌篤、磯部稔、西川俊夫
  • Organizer: 第46回天然化学談話会
  • Place of Presentation: 熱川
  • Year and Date: 20110707-09
• [Presentation] 薬用植物由来の多環性天然物polygalolide Aの全合成 (2011)
  • Author(s): 山田ひと美、安立昌篤、磯部稔、西川俊夫
  • Organizer: 第9回次世代を担う有機化学シンポジウム
  • Place of Presentation: 東京
  • Year and Date: 20110527-28
• [Presentation] 6, 11-トリデオキシテトロドトキシンの全合成 (2011)
  • Author(s): 榊原良、安立昌篤、磯部稔、西川俊夫
  • Organizer: 日本農芸化学会2011年度大会
  • Place of Presentation: 京都
  • Year and Date: 20110326-28
• [Presentation] ソラノエクレピンA左側部分の合成研究 (2011)
  • Author(s): 鳥居真衣、安立昌篤、西川俊夫
  • Organizer: 日本農芸化学会2011年度大会
  • Place of Presentation: 京都
  • Year and Date: 20110326-28
• [Presentation] 分子内C-グリコシル化反応を利用したPolygalolide Aの全合成 (2011)
  • Author(s): 山田ひと美、安立昌篤、磯部稔、西川俊夫
  • Organizer: 日本農芸化学会2011年度大会
  • Place of Presentation: 京都
  • Year and Date: 20110326-28
• [Presentation] 薬用植物由来の多環性化合物ポリガロリドAの化学合成 (2011)
  • Author(s): 山田ひと美、安立昌篤、磯部稔、西川俊夫
  • Organizer: 2011年度名古屋大学若手女性研究者サイエンスフォーラム
  • Place of Presentation: 名古屋
  • Year and Date: 2011-11-29
• [Presentation] Total Synthesis of Polygalolide A by Intramolecular C-Glycosylation (2011)
  • Author(s): Hitomi Yamada, Masaatsu Adachi, Minoru Isobe, Toshio Nishikawa
  • Organizer: Nagoya University Global COE-RCMS International Symposium on Organic Chemistry and 7th Yoshimasa Hirata Memorial Lecture
  • Place of Presentation: Nagoya, Japan
  • Year and Date: 2011-03-17
• [Presentation] A New Synthetic Approach to Oxabicyclo[3. 2. 1] octene Skeleton by Intramolecular C-Glycosylation (2010)
  • Author(s): Hitomi Yamada, Masaatsu Adachi, Minoru Isobe, Toshio Nishikawa
  • Organizer: 2010 International Chemical Congress of Pacific Basin Societies(PACIFICHEM2010)
  • Place of Presentation: Honolulu, U. S. A
  • Year and Date: 20101215-20
• [Presentation] Synthetic Studies on Solanoeclepin A, a Substance Causing Hatching Phenomenon Toward Potato Cyst Nematodes (2010)
  • Author(s): Takema Komada, Masaatsu Adachi, Toshio Nishikawa
  • Organizer: 2010 International Chemical Congress of Pacific Basin Societies(PACIFICHEM2010)
  • Place of Presentation: Bangkok, Thailand
  • Year and Date: 20101208-09
• [Presentation] Synthetic Studies on Polygalolides Isolated from a Medicinal Plant (2010)
  • Author(s): Masaatsu Adachi, Hitomi Yamada, Minoru Isobe, Toshio Nishikawa
  • Organizer: The 9th NRCT-JSPS Joint Seminar 2010 "Natural Medicine Research for the Next Decade : New Challenges and Furture Collaboration"
  • Place of Presentation: Bangkok, Thailand
  • Year and Date: 20101208-09
• [Presentation] Synthetic Studies on Biologically Active Natural Products (2010)
  • Author(s): oshio Nishikawa, Kumi Sugino, Atsuo Nakazaki, Keiko Higuchi, Masaatsu Adachi, Nopporn Thasana, Minoru Isobe
  • Organizer: The 9th NRCT-JSPS Joint Seminar 2010 "Natural Medicine Research for the Next Decade : New Challenges and Furture Collaboration
  • Place of Presentation: Bangkok, Thailan
  • Year and Date: 20101208-09
• [Presentation] Multi-functionality of N-Trichloroacetyl Group Developed in the Synthesis of Tetrodotoxin and its Analogues (2010)
  • Author(s): Toshio Nishikawa, Masaatsu Adachi, Ryo Sakakibara, Yoshiki Satake, Minoru Isobe
  • Organizer: The 5th International Conference on Cutting-edge Organic Chemistry in Asia(ICCEOCA-5), The 1st New phase International Conference on Cutting-edge Organic Chemistry in Asia
  • Place of Presentation: Hsinchu, Taiwan
  • Year and Date: 20101107-11
• [Presentation] Total Synthesis of Polygalolide A (2010)
  • Author(s): Masaatsu Adachi, Hitomi Yamada, Minoru Isobe, Toshio Nishikawa
  • Organizer: The Pre-Symposium of 5th International Conference on Organic Chemistry in Asia
  • Place of Presentation: Kaohsiung, Taiwan
  • Year and Date: 20101105-07
• [Presentation] 分子内C-グリコシル化反応を利用したpolygalolide類の合成研究 (2010)
  • Author(s): 山田ひと美、安立昌篤、磯部稔、西川俊夫
  • Organizer: 第52回天然有機化合物討論会
  • Place of Presentation: 静岡
  • Year and Date: 20100929-1001
• [Presentation] Synthetic Studies on Solanoeclepin A, Causing Hatching Phenomenon Toward Potato Cyst Nematodes (2010)
  • Author(s): 駒田武馬、安立昌篤、西川俊夫
  • Organizer: 第4回リトリート『Labo-Net』
  • Place of Presentation: 豊橋
  • Year and Date: 20100914-15
• [Presentation] 5, 6, 11-トリデオキシテトロドトキシンの全合成 (2010)
  • Author(s): 榊原良、佐竹佳樹、安立昌篤、磯部稔、西川俊夫
  • Organizer: 第45回天然物化学談話会
  • Place of Presentation: 蒲郡
  • Year and Date: 20100706-08
• [Presentation] 薬用植物由来の多環性天然物ポリガロリドの合成研究 (2010)
  • Author(s): 山田ひと美、安立昌篤、磯部稔、西川俊夫
  • Organizer: 第45回天然物化学談話会
  • Place of Presentation: 蒲郡
  • Year and Date: 20100706-08
• [Presentation] Synthetic Studies on Polygalolides (2010)
  • Author(s): 安立昌篤
  • Organizer: 第1回有機分子構築法夏の勉強会
  • Place of Presentation: 仙台
  • Year and Date: 20100522-23
• [Presentation] ジャガイモシスト線虫孵化促進物質ソラノエクレピンAの合成研究 (2010)
  • Author(s): 鳥居真衣、安立昌篤、西川俊夫
  • Organizer: 日本農芸化学会中部支部第159回例会
  • Place of Presentation: 名古屋
  • Year and Date: 2010-10-30
• [Presentation] 新規グリコシル化反応を利用したPolygalolide類の合成研究 (2010)
  • Author(s): 安立昌篤、山田ひと美、磯部稔、西川俊夫
  • Organizer: 糖鎖科学名古屋拠点第8回「若手の力」フォーラム
  • Place of Presentation: 名古屋
  • Year and Date: 2010-09-06
• [Remarks]
  • URL: http://www.agr.nagoya-u.ac.jp/~organic/