Efficient Synthesis of Marine Polycyclic Ethers

2009 Fiscal Year Final Research Report

• Project/Area Number: 19350023
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Okayama University
• Principal Investigator: KADOTA Isao Okayama University, 大学院・自然科学研究科, 教授 (30250666)
• Co-Investigator(Kenkyū-buntansha): TAKAMURA Hiroyoshi 岡山大学, 大学院・自然科学研究科, 助教 (70422798)
• Project Period (FY): 2007 – 2009
• Keywords: 合成有機化学 / 天然有機化合物

Research Abstract

In recent years there has been an explosion of interest in biologically active natural products of marine origin. Due to their structural novelty and toxicity, polycyclic ethers isolated from marine algae are particularly attractive targets for synthetic chemists. Since further biological studies are hampered by the limited availability from nature, chemical synthesis has been the sole realistic way to obtain sufficient amounts of the polycyclic ethers. In this study, convergent synthesis of brevenal and ciguatoxin CTX3C via the intramolecular allyaltion followed by ring-closing metathesis were examined.

Research Products

• [Journal Article] Stereoselective synthesis of the C14-C24 degraded fragment of symbiodinolide. (2010)
  • Author(s): Takamura, H., Kadonaga, Y., Kadota, I., Uemura, D.
  • Journal Title: Tetrahedron Lett. 51,(19) Pages: 2603-2605
• [Journal Article] Convergent synthesis of the A-E ring segment of ciguatoxin CTX3C. (2009)
  • Author(s): Kadota, I., Abe, T., Uni, M., Takamura, H., Yamamoto, Y.
  • Journal Title: Tetrahedron 65,(37) Pages: 7784-7789
• [Journal Article] Stereoselective synthesis and absolute configuration of the C33-C42 fragment of symbiodinolide. (2009)
  • Author(s): Takamura, H., Kadonaga, Y., Yamano, Y., Han, C., Kadota, I., Uemura, D.
  • Journal Title: Tetrahedron 65,(36) Pages: 7449-7456
• [Journal Article] Stereoselective Synthesis and Absolute Configuration of the C1'-C25' Fragment of Symbiodinolide. (2009)
  • Author(s): Takamura, H., Murata, T., Asai, T., Kadota, I., Uemura, D.
  • Journal Title: J. Org. Chem. 74,(17) Pages: 6658-6666
• [Journal Article] Selective cleavage of primary MPM ethers with TMSI/Et3N. (2009)
  • Author(s): Kadota, I., Yamagami, Y., Fujita, N., Takamura, H.
  • Journal Title: Tetrahedron Lett. 50,(31) Pages: 4552-4553
• [Journal Article] Synthesis and Structural Revision of Symbiodinolide C23-C34 Fragment. (2009)
  • Author(s): Murata, T., Sano, M., Takamura, H., Kadota, I., Uemura, D.
  • Journal Title: J. Org. Chem. 74,(13) Pages: 4797-4803
• [Journal Article] Total Synthesis of Brevenal. (2009)
  • Author(s): Takamura, H., Kikuchi, S., Nakamura, Y., Yamagami, Y., Kishi, T., Kadota, I., Yamamoto, Y.
  • Journal Title: Org. Lett. 11,(12) Pages: 2531-2534
• [Journal Article] A transannular Diels-Alder strategy for the construction of the CDE ring system of nakiterpiosin. (2009)
  • Author(s): Takamura, H., Yamagami, Y., Ito, T., Ito, M., Arimoto, H., Kadota, I., Uemura, D.
  • Journal Title: Heterocycles 77,(1) Pages: 351-364
• [Journal Article] Synthesis and structural determination of the C33-C42 fragment of symbiodinolide. (2009)
  • Author(s): Takamura, H., Kadonaga, Y., Yamano, Y., Han, C., Aoyama, Y., Kadota, I., Uemura, D.
  • Journal Title: Tetrahedron Lett. 50,(8) Pages: 863-866
• [Journal Article] Stereocontrolled synthesis of the C79-C96 fragment of symbiodinolide. (2008)
  • Author(s): Takamura, H., Ando, J., Abe, T., Murata, T., Kadota, I., Uemura, D.
  • Journal Title: Tetrahedron Lett. 49,(31) Pages: 4626-4629
• [Journal Article] A cross-metathesis approach to the stereocontrolled synthesis of the AB ring segment of ciguatoxin. (2008)
  • Author(s): Kadota, I., Abe, T., Uni, M., Takamura, H., Yamamoto, Y.
  • Journal Title: Tetrahedron Lett. 49,(22) Pages: 3643-3647
• [Journal Article] Solvent-Controlled Stereoselective Formation of a Cyclic Ether in the Lewis Acid-Mediated Allylation of anα-Chloroacetoxy Acyclic Ether. Very High Stereoselectivity in CH3CN vs Low Stereoselectivity in CH2Cl2. (2007)
  • Author(s): Gridnev, I.D., Kikuchi, S., Touchy, A.S., Kadota, I., Yamamoto, Y.
  • Journal Title: J. Org. Chem. 72,(22) Pages: 8371-8375
• [Presentation] シガトキシンCTX3CのHIJKLM環部の合成研究 (2010)
  • Author(s): 阿部享史
  • Organizer: 日本化学会第90春期年会
  • Place of Presentation: 大阪
  • Year and Date: 2010-03-28
• [Presentation] シガトキシンCTX3CのEFGH環部の合成研究 (2010)
  • Author(s): 藤田直弥
  • Organizer: 日本化学会第90春期年会
  • Place of Presentation: 大阪
  • Year and Date: 2010-03-28
• [Presentation] 海洋産天然物ブレベナールの全合成 (2009)
  • Author(s): 門田功
  • Organizer: 2009年日本化学会西日本大会
  • Place of Presentation: 松山
  • Year and Date: 2009-11-07
• [Presentation] ブレベナールの全合成 (2009)
  • Author(s): 山神雄司
  • Organizer: 第51回天然有機化合物討論会
  • Place of Presentation: 名古屋
  • Year and Date: 2009-10-09
• [Presentation] ブレベナールの全合成 (2009)
  • Author(s): 山神雄司
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 船橋
  • Year and Date: 2009-03-29
• [Presentation] 海洋産ポリ環状エーテルの合成戦略 (2008)
  • Author(s): 門田功
  • Organizer: 第24回若手化学者のための化学道場
  • Place of Presentation: 徳島
  • Year and Date: 2008-09-11
• [Presentation] Convergent Synthesis of Marine Polycyclic Ethers (2008)
  • Author(s): 門田功
  • Organizer: 5th International Symposium on Integrated Synthesis
  • Place of Presentation: 神戸
  • Year and Date: 2008-09-05
• [Presentation] シガトキシンCTX3CのA-E環部の合成研究 (2008)
  • Author(s): 阿部享史
  • Organizer: 日本化学会第88春季年会
  • Place of Presentation: 東京
  • Year and Date: 2008-03-28
• [Remarks]
  • URL: http://chem.okayama-u.ac.jp/~organic/homejpn.html