Synthesis of functionalized cycloalkene by transformation of glycal and synthetic study on bioactive natural product.

• Project/Area Number: 20780082
• 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 Nagoya University, 大学院・生命農学研究科, 助教 (80432251)
• Project Period (FY): 2008 – 2009
• Project Status: Completed (Fiscal Year 2009)
• Budget Amount: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000); Fiscal Year 2009: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000); Fiscal Year 2008: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
• Keywords: 天然物化学 / 有機化学 / 合成化学 / 糖

Research Abstract

Synthesis of the functionalized cycloalkene skeleton has been developed through transformation of substituted glycal. The glycal with great diversity of functionality played a crucial role in this reaction not only for the conformational flexibility but also for synthesis of a functionalized cycloalkene ring system.

Research Products

• [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. Jpn. 83 Pages: 66-68
  • NAID: 10027171500
  • Peer Reviewed
• [Journal Article] Synthesis of an Advanced Intermediate Bearing Two Hydroxy Groups for (-)-Tetrodotoxin and Its Analogs. (2010)
  • Author(s): Toshio Nishikawa, Yuya Koide, Masaatsu Adachi, Minoru Isobe
  • Journal Title: Bull.Chem.Soc.Jpn Pages: 66-68
  • NAID: 10027171500
  • Peer Reviewed
• [Journal Article] Novel Stereocontrolled Synthesis of Highly-functional i zed Cyclobutanes by Epoxide Opening through a Carbanion Intermediate in Heteroconjugate Addition. (2009)
  • Author(s): Adachi, M.; Yamauchi, E.; Komada, T.; Isobe, M.
  • Journal Title: Synlett Pages: 1157-1161
  • Peer Reviewed
• [Journal Article] Novel Stereocontrolled Synthesis of Highly Functionalized Cyclobutane by Epoxide Opening through a carbanion Intermediate in Heteroconjugate Addition. (2009)
  • Author(s): Masaatsu Adachi, Eiji Yamauchi, Takema Komada, Minoru Isobe
  • Journal Title: Synlett Pages: 1157-1161
  • Peer Reviewed
• [Journal Article] Novel Stereocontrolled Synthesis of Highly Functionalized Cyclobutane by Epoxide Opening through a carbanion Intermediate in Heteroconjugate Addition (2009)
  • Author(s): Masaatsu Adachi
  • Journal Title: Synlett Pages: 1157-1161
  • Peer Reviewed
• [Journal Article] Streptomyces Phospholipase D Mutants with Altered Substrate Speoificity Capable of Phosphatidylinositol Synthesis. (2008)
  • Author(s): Masayama, A.; Takahashi, T.; Tsukada, K.; Nishikawa, S.; Takahashi, R.; Adachi, M.; Koga, K.; Suzuki, A.; Yamane, T.; Nakano, H.; Iwasaki, Y.
  • Journal Title: ChemBioChem 9 Pages: 974-981
  • Peer Reviewed
• [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2010年度大会
  • Place of Presentation: 東京
• [Presentation] 分子内C-グリコシル化反応を利用したポリガロリドの合成研究 (2010)
  • Author(s): 山田ひと美、安立昌篤、西川俊夫、磯部稔
  • Organizer: 日本農芸化学会2010年度大会
  • Place of Presentation: 東京
• [Presentation] 破骨細胞形成阻害物質チャキシンの合成研究 (2009)
  • Author(s): 安立昌篤、卜部直樹、西川俊夫
  • Organizer: 日本農芸化学会第156回中部支部例会
  • Place of Presentation: 名古屋
  • Year and Date: 2009-10-03
• [Presentation] シガトキシンの全合成 (2009)
  • Author(s): 濱嶋祥就、馬場貴之、藤井泰志、細川誠二郎、黄国賓、池盛文数、吉良和信、Klirschbaum Bettina、野々山彰人、劉同 柱、Saeeng Rungnapha、沢田直隆、高井繁幸、田中成佳、Yenjai Chavi、安立昌篤、西川俊夫、磯部稔
  • Organizer: 第51回天然有機化合物討論会
  • Place of Presentation: 名古屋
• [Presentation] ヘテロ共役付加反応を用いた多官能基化シクロブタンの立体制御合成 (2009)
  • Author(s): 安立昌篤
  • Organizer: 第44回天然物化学談話会
  • Place of Presentation: 筑波
• [Presentation] 分子内C-グリコシル化反応を利用したポリガロリドの合成研究 (2009)
  • Author(s): 山田ひと美、安立昌篤、西川俊夫、磯部稔
  • Organizer: 日本農芸化学会2009年度大会
  • Place of Presentation: 福岡
• [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 (2009)
  • Author(s): 駒田武馬、安立昌篤、西川俊夫、磯部稔
  • Organizer: 日本農芸化学会2009年度大会
  • Place of Presentation: 福岡
• [Presentation] Stereocontrolled Synthesis of Highly-functionalized Cyclobutane Through Heteroconjugate Addition (2008)
  • Author(s): Masaatsu Adachi, Takema Komada, Eiji Yamauchi, Minoru Isobe.
  • Organizer: The 22nd Naito Conference on Chemical Biology [I]
  • Place of Presentation: Sapporo, Japan
• [Presentation] Stereocontrolled Synthesis of Highly-functionalized Cyclobutane Through Heteroconjugate Addition. (2008)
  • Author(s): Masaatsu Adachi, Takema Komada, Eiji Yamauchi, Minoru Isobe.
  • Organizer: IUPAC IC0S-17
  • Place of Presentation: Daejeon, Korea
• [Presentation] Stereocontrolled Synthesis of Highly-functionalized Cyclobutane Through Heteroconjugate Addition (2008)
  • Author(s): Masaatsu Adachi
  • Organizer: IUPAC ICOS-17
  • Place of Presentation: Daejeon, Korea
• [Book] Glycoscience, 2^<nd> edition (2009)
  • Author(s): Masaatsu Adachi
  • Total Pages: 57
  • Publisher: Springer-Verlag
• [Book] Glycoscience(C-Glycosylation, Cheimical Glycosylation Reactions, 2nd edition) (2008)
  • Author(s): Nishikawa, T.;Adachi, M.;Isobe, M.
  • Publisher: Springer Verlag
• [Remarks]
  • URL: http://www-agr.nagoya-u.ac,jp/~organic/