Synthetic Studies on biologically active natural products containing novel heterocyclic structures

2011 Fiscal Year Final Research Report

• Project/Area Number: 20380067
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Bioproduction chemistry/Bioorganic chemistry
• Research Institution: Nagoya University
• Principal Investigator: NISHIKAWA Toshio 名古屋大学, 生命農学研究科, 教授 (90208158)
• Co-Investigator(Kenkyū-buntansha): ADACHI Masaatsu 名古屋大学, 大学院・生命農学研究科, 助教 (80432251) ; NAKAZAKI Atsuo 名古屋大学, 大学院・生命農学研究科, 准教授 (00366428)
• Project Period (FY): 2008 – 2011
• Keywords: 有機合成 / ヘテロ環 / β-ラクタム / チャルテリン / パクタマイシン / タゲチトキシン

Research Abstract

Synthetic methodologies of natural products containing novel heterocyclic structures have been developed ; synthetic routes of the skeletons of pactamycin and tagetitoxin were established, and total synthesis of decarbamoyl-α-saxitoxinol and polygalolide A was achieved.

Research Products

• [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] 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] Dynamic Chirality Determines Critical Roles for Bioluminescence in Symplectin-Dehydrocoelenterazine System (2011)
  • Author(s): Kongjinda, V.; Nakashima, Y.; Tani, N.; Kuse, M.; Nishikawa, T.; Yu, C.-H.; Harada, N.; Isobe, M.
  • Journal Title: Chem. Asian J. Volume: 6 Pages: 2080-2091
  • DOI: doi:10.1002/asia.201100089
  • Peer Reviewed
• [Journal Article] Total Synthesis of Polygalolode 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 Synthetic Route to the Saxitoxin Skeleton : Synthesis of Decarbamoylα-Saxitoxinol, an Analogue of Saxitoxin Produced by the Cyanobacterium (2011)
  • Author(s): Sawayama, Y.; Nishikawa, T.
  • Journal Title: Lyngbya wollei. Angew. Chem. Int. Ed. Volume: 50 Pages: 7176-7178
  • DOI: doi:10.1002/anie.201102494
  • 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: J. Org. Chem. Volume: 76 Pages: 6942-6945
  • DOI: doi:10.1021/jo201153h
  • Peer Reviewed
• [Journal Article] Concise Synthesis of Deformylflustrabromine, a Marine Indole Alkaloid, Through a Propargyl Dicobalt Hexacarbonyl Complex (2011)
  • Author(s): Isaji, H.; Nakazaki, A.; Isobe, M.; Nishikawa, T
  • Journal Title: Chem. Lett. Volume: 40 Pages: 1079-1081
  • DOI: doi:10.1246/cl.2011.1079
  • Peer Reviewed
• [Journal Article] Synthetic Study on Sespendole, an Indole Sesquiterpene Alkaloid : Stereocontrolled Synthesis of the Sesquiterpene Segment Bearing All Requisite Stereogenic Centers (2011)
  • Author(s): Sugino, K.; Nakazaki, A.; Isobe, M.; Nishikawa, T
  • Journal Title: Synlett Pages: 647-650
  • DOI: Doi:10.1055/s-0030-1259546
  • Peer Reviewed
• [Journal Article] Bromocyclization of Alkynyl Guanidine : A New Approach to the Synthesis of Cyclic Guanidines of Saxitoxin (2011)
  • Author(s): Sawayama, Y.; Nishikawa, T
  • Journal Title: Synlett Pages: 651-654
  • DOI: Doi:10.1055/s-0030-1259551
  • Peer Reviewed
• [Journal Article] Scalable Synthesis of a New Dihydroxylated Intermediate for Tetrodotoxin and Its Analogues (2010)
  • Author(s): Satake, Y.; Nishikawa, T.; Hiramatsu, T.; Araki, H.; Isobe, M
  • Journal Title: Synthesis Pages: 1992-1998
  • DOI: Doi:10.1055/s-0029-1218747
  • Peer Reviewed
• [Journal Article] Synthesis of N-Acylisoxazolidine Derivatives, Related to a Partial Structure Found in Zetekitoxin AB, a Golden Frog Poison. (2009)
  • Author(s): Nishikawa, T.; Urabe, D.; Isobe, M.
  • Journal Title: Heterocycles Volume: 79 Pages: 379-385
  • DOI: DOI:10.3987/COM-08-S(D)44
  • Peer Reviewed
• [Journal Article] Substituent Effect of Imino-O-arenesulfonates, a Coupling Partner in Suzuki-Miyaura Reaction for Substitution of the Pyrazine Ring : A Study for the Synthesis of Coelenterazine Analogs. (2009)
  • Author(s): Makarasen, A.; Kuse, M.; Nishikawa, T.; Isobe, M.
  • Journal Title: Bull. Chem. Soc. Jpn. Volume: 82 Pages: 870-878
  • DOI: Doi:10.1246/bcsj.82.870
  • Peer Reviewed
• [Journal Article] Selective Oxidation by the Hydroperoxide in the Photoprotein, Aequorin. (2009)
  • Author(s): Doi, I.; Kuse, M.; Nishikawa, T.; Isobe, M.
  • Journal Title: Bioorg. Med. Chem. Volume: 17 Pages: 3399-3404
  • DOI: doi:10.1016/j.bmc.2009.03.033
  • Peer Reviewed
• [Journal Article] Synthesis of Four Lysine-Linked Cereulide Analogues Showing Ionophoric Activity Towards Potassium Cations as Lead Compounds for Emetic Toxin-Detection by Immunoassays (2009)
  • Author(s): Makarasen, A.; Nishikawa, T.; Isobe, M.
  • Journal Title: Synthesis Pages: 2184-2204
  • DOI: Doi:10.1055/s-0029-1216837
  • Peer Reviewed
• [Journal Article] Dehydrocoelenterazine Is the Organic Substance Constituting the Prosthetic Group of Pholasin (2009)
  • Author(s): Tanaka, E.; Kuse, M.; Nishikawa, T.
  • Journal Title: ChemBioChem Volume: 10 Pages: 2725-2729
  • DOI: DOI:10.1002/cbic.200900503
  • Peer Reviewed
• [Journal Article] Synthesis of N-Hydroxyenamide by N-Acylation of Oxime Derivative for Synthesis of Chartelline, a Novel Marine Alkaloid (2008)
  • Author(s): Kajii, S.; Nishikawa, T.; Isobe, M.
  • Journal Title: Tetrahedron Lett. Volume: 49 Pages: 594-597
  • DOI: doi:10.1016/j.tetlet.2007.11.155
  • Peer Reviewed
• [Journal Article] Synthetic studies and biosynthetic speculation on marine alkaloid chartelline (2008)
  • Author(s): Kajii, S.; Nishikawa, T.; Isobe, M.
  • Journal Title: Chem. Commun. Pages: 3121-3123
  • DOI: DOI:10.1039/B803797C
  • Peer Reviewed
• [Journal Article] Regioselectivity of Larock Indol Synthesis Using Functionalized Alkynes. (2008)
  • Author(s): Sugino, K.; Yoshimura, H.; Nishikawa, T.; Isobe, M.
  • Journal Title: Biosci. Biotechnol. Biochem. Volume: 72 Pages: 2092-2102
  • DOI: Doi:10.1271/bbb.8017
  • Peer Reviewed
• [Presentation] イオンチャネル阻害剤の創製を目指した海産天然毒の化学合成 (2012)
  • Author(s): 西川俊夫
  • Organizer: シンポジウム4SY09「天然物ケミカルバイオロジー」日本農芸化学会2012年度大会
  • Place of Presentation: 京都
  • Year and Date: 2012-03-25
• [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] A New Synthetic Route to the Saxitoxin Skelton (2011)
  • Author(s): Toshio Nishikawa, Yusuke Sawayama
  • 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
  • Year and Date: 20111211-15
• [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] Decarbamoyl-α-saxitoxinolの合成 (2011)
  • Author(s): 澤山裕介、西川俊夫
  • Organizer: 第53回天然有機化合物討論会
  • Place of Presentation: 大阪
  • Year and Date: 20110927-29
• [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] テトロドトキシン類の化学合成とフグ毒の謎。『That's応用生命科学』有機化学、分子生物学、食品科学の最新研究から見る応用生命科学のいま。 (2011)
  • Author(s): 西川俊夫
  • Organizer: 日本農芸化学会中部支部第161回例会
  • Place of Presentation: 岐阜
  • Year and Date: 2011-06-18
• [Presentation] 含窒素生理活性天然物の合成イオンチャネルを阻害する天然毒素とその類縁体の化学合成- (2011)
  • Author(s): 西川俊夫
  • Organizer: 新規素材探索研究会第10回セミナー
  • Place of Presentation: 横浜
  • Year and Date: 2011-06-10
• [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(PACIFICHEM 2010)
  • Place of Presentation: Honolulu, U.S.A.
  • Year and Date: 20101215-20
• [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 Solanoeclepin A, a Substance Causing Hatching Phenomenon Toward Potato Cyst Nematodes (2010)
  • Author(s): Takema Komada, Masaatsu Adachi, 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] 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] テトロドトキシンの合成-古くて新しい天然物の合成- (2010)
  • Author(s): 西川俊夫
  • Organizer: 20周年記念万有福岡シンポジウム
  • Place of Presentation: 福岡
  • Year and Date: 2010-05-22
• [Presentation] A Novel Reverse Prenylation of Indole Derivatives by means of Acetylene Cobalt Complex. (2009)
  • Author(s): Toshio Nishikawa, Hisaaki Isaji, Atsuo Nakazaki, Minoru Isobe
  • Organizer: The 4th International Conference on Cutting-Edge Organic Chemistry in Asia
  • Place of Presentation: Bangkok, Thailand
  • Year and Date: 20091129-1203
• [Presentation] Synthetic Studies on Marine Alkaloid Chartelline (2009)
  • Author(s): Toshio Nishikawa
  • Organizer: The International Start-up Conference of Cutting-edge Organic Chemistry in Asia(II)
  • Place of Presentation: Chiba, Japan
  • Year and Date: 20090810-11
• [Presentation] Synthetic Studies on Naturally Occuring Sesquiterpene Indole Alkaloide (2009)
  • Author(s): Kumi Sugino, Toshio Nishikawa, Minoru Isobe
  • Organizer: The 8th NRCT-JSPS Joint Seminar : Innovative Research in Natural Products for Sustainable Development
  • Place of Presentation: Bangkok, Thailand
  • Year and Date: 20090203-04
• [Presentation] Synthesis Studies on Naturally Occurring Heterocycles (2009)
  • Author(s): Toshio Nishikawa, Yoshiki Satake, Hisaaki Isaji, Minoru Isobe
  • Organizer: The 8th NRCT-JSPS Joint Seminar : Innovative Research in Natural Products for Sustainable Development
  • Place of Presentation: Bangkok, Thailand
  • Year and Date: 20090203-04
• [Presentation] ヘテロ環天然物の全合成研究ー天然物全合成は新反応発見の場となるか? (2009)
  • Author(s): 西川俊夫
  • Organizer: 平成21年度有機合成化学協会東海支部有機合成セミナー
  • Place of Presentation: 静岡
  • Year and Date: 2009-09-12
• [Presentation] 多官能基性天然物の合成研究ーフグ毒テトロドトキシンの更に効率よい合成法を求めてー (2008)
  • Author(s): 西川俊夫
  • Organizer: 第39回中部化学関係学協会支部連合秋季大会特別討論会[有機合成化学](触媒反応と全合成)
  • Place of Presentation: 名古屋
  • Year and Date: 20081108-09
• [Presentation] 5-デオキシテトロドトキシンの全合成研究 (2008)
  • Author(s): 佐竹佳樹、西川俊夫、磯部稔
  • Organizer: 第94回有機合成シンポジウム
  • Place of Presentation: 東京
  • Year and Date: 20081107-08
• [Presentation] Total Synthesis of 5-Deoxytetrodotoxin, A Plausible Biosynthetic Precursor for Tetrodotoxin (2008)
  • Author(s): Toshio Nishikawa, Yoshiki Satake, Minoru Isobe
  • Organizer: The 3rd International Conference on Cutting-Edge Organic Chemistry in Asia
  • Place of Presentation: Hangzhou, China
  • Year and Date: 20081019-23
• [Presentation] Studies for Biosynthesis and Food Chain Mechanism of Tetrodotoxin by using its Synthetic probes (2008)
  • Author(s): Toshio Nishikawa, Yoshiki Satake, Minoru Isobe
  • Organizer: The 22nd Naito Conference on Chemical Biology[I]
  • Place of Presentation: Sapporo, Japan
  • Year and Date: 20080909-12
• [Presentation] フグ毒テトロドトキシンの合成研究から学んだ天然物合成の魅力 (2008)
  • Author(s): 西川俊夫
  • Organizer: 理研シンポジウム「第9回分析・解析技術と化学の最先端」
  • Place of Presentation: 埼玉
  • Year and Date: 2008-12-09
• [Book] Claisen転位(1)「天然物合成で活躍した反応-実験のコツとポイント。有機合成化学協会編 (2011)
  • Author(s): 大藪紀雄、西川俊夫
  • Total Pages: 102-103
  • Publisher: 化学同人
• [Book] C-Glycosylation, Chemical Glycosylation Reactions, In Glycoscience, 2nd edition (2008)
  • Author(s): Nishikawa, T.; Adachi, M.; Isobe, M.
  • Total Pages: 756-811
  • Publisher: Springer Verlag
• [Remarks]
  • URL: http://www.agr.nagoya-u.ac.jp/~organic/