Efficient Synthesis of Marine Polycyclic Ethers

• 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
• Project Status: Completed (Fiscal Year 2009)
• Budget Amount: ¥19,110,000 (Direct Cost: ¥14,700,000、Indirect Cost: ¥4,410,000); Fiscal Year 2009: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000); Fiscal Year 2008: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000); Fiscal Year 2007: ¥9,490,000 (Direct Cost: ¥7,300,000、Indirect Cost: ¥2,190,000)
• Keywords: 合成有機化学 / 天然有機化合物 / 海洋産天然物 / ポリ環状エーテル / 収束的合成 / 分子内アリル化 / 閉環メタセシス / 全合成 / ブレベナール / シガトキシン / 海産天然物 / 収束適合性

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
  • NAID: 110009757645
• [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] Convergent synthesis of the A-E ring segment of ciguatoxin CTX3C (2009)
  • Author(s): Isao Kadota
  • Journal Title: Tetrahedron 65 Pages: 7784-7789
  • Peer Reviewed
• [Journal Article] Stereoselective synthesis and absolute configuration of the C33-C42 fragment of symbiodinolide (2009)
  • Author(s): Hiroyoshi Takamura
  • Journal Title: Tetrahedron 65 Pages: 7449-7456
  • Peer Reviewed
• [Journal Article] Stereoselective Synthesis and Absolute Configuration of the C1'-C25' Fragment of Symbiodinolide (2009)
  • Author(s): Hiroyoshi Takamura
  • Journal Title: Journal of Organic Chemistry 74 Pages: 6658-6666
  • Peer Reviewed
• [Journal Article] Selective cleavage of primary MPM ethers with TMSI/Et3N (2009)
  • Author(s): Isao Kadota
  • Journal Title: Tetrahedron Letters 50 Pages: 4552-4553
  • Peer Reviewed
• [Journal Article] Total Synthesis of Brevenal (2009)
  • Author(s): Hiroyoshi Takamura
  • Journal Title: Organic Letters 11 Pages: 2531-2534
  • NAID: 110009757645
  • Peer Reviewed
• [Journal Article] A transannular Diels-Alder strategy for the construction of the CDE ring system of nakiterpiosin (2009)
  • Author(s): Hiroyoshi Takamura
  • Journal Title: Heterocycles 77 Pages: 351-364
  • Peer Reviewed
• [Journal Article] Synthesis and structural determination of the C33-C42 fragment of symbiodinolide (2009)
  • Author(s): Hiroyoshi Takamura
  • Journal Title: Tetrahedron Letters 50 Pages: 863-866
  • Peer Reviewed
• [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
  • NAID: 120002306949
• [Journal Article] A Cross-metathesis Approach to the Stereocontrolled Synthesis of the AB Ring Segment of Ciguatoxin (2008)
  • Author(s): I. Kadota
  • Journal Title: Tetrahedron Letters 49 Pages: 3643-3647
  • NAID: 120002306949
  • Peer Reviewed
• [Journal Article] Stereocontrolled Synthesis of the C79-C96 Fragment of Symbiodinolide (2008)
  • Author(s): H. Takamura
  • Journal Title: Tetrahedron Letters 49 Pages: 4626-4629
  • Peer Reviewed
• [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
• [Journal Article] A Convergent Approach to the Formal Total Synthesis of Hemibrevetoxin B (2007)
  • Author(s): I. Kadota
  • Journal Title: Tetrahedron Letters 48 Pages: 219-221
  • Peer Reviewed
• [Journal Article] ブレベトキシンBの全合成 (2007)
  • Author(s): 門田 功
  • Journal Title: 有機合成化学協会誌 65 Pages: 430-438
  • NAID: 10020137685
  • Peer Reviewed
• [Journal Article] Solvent-Controlled Stereoselective Formation of a Cyclic Ether in the Lewis Acid-Mediated Allylation of an α-Chloroacetoxy Acyclic Ether. Very High Stereoselectivity in CH_3CN vs Low Stereoselectivity in CH_2Cl_2 (2007)
  • Author(s): I.D. Gridnev
  • Journal Title: The Journal of Organic Chemistry 71 Pages: 8371-8375
  • Peer Reviewed
• [Journal Article] Formal Total Synthesis of Hemibrevetoxin B via the Intramolecular Allylation Followed by Ring-closing Metathesis (2007)
  • Author(s): I. Kadota
  • Journal Title: Heterocycles 74 Pages: 617-627
  • NAID: 40015919615
  • Peer Reviewed
• [Presentation] シンビオジノライドC14-C24フラグメントの立体選択的合成 (2010)
  • Author(s): 角永悠一郎
  • Organizer: 日本化学会第90春期年会
  • Place of Presentation: 近畿大学本部キャンパス(大阪府)
  • Year and Date: 2010-03-29
• [Presentation] シンビオジノライドC94-C104フラグメントの合成研究 (2010)
  • Author(s): 津田浩輔
  • Organizer: 日本化学会第90春期年会
  • Place of Presentation: 近畿大学本部キャンパス(大阪府)
  • Year and Date: 2010-03-29
• [Presentation] 縮環エーテル類に対する新規核間メチル基導入法 (2010)
  • Author(s): 岸敬之
  • Organizer: 日本化学会第90春期年会
  • Place of Presentation: 近畿大学本部キャンパス(大阪府)
  • Year and Date: 2010-03-29
• [Presentation] ピラニシンの全合成 (2010)
  • Author(s): 山神雄司
  • Organizer: 日本化学会第90春期年会
  • Place of Presentation: 近畿大学本部キャンパス(大阪府)
  • Year and Date: 2010-03-29
• [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] 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: 近畿大学本部キャンパス(大阪府)
  • Year and Date: 2010-03-28
• [Presentation] シガトキシンCTX3CのE環部の合成 (2010)
  • Author(s): 佐藤優樹
  • Organizer: 日本化学会第90春期年会
  • Place of Presentation: 近畿大学本部キャンパス(大阪府)
  • 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: 近畿大学本部キャンパス(大阪府)
  • Year and Date: 2010-03-28
• [Presentation] Total Synthesis of Brevenal (2009)
  • Author(s): Isao Kadota
  • Organizer: The 11th International Kyoto Conference on New Aspects of Organic Chemistry(IKCOC-11)
  • Place of Presentation: リーグロイヤルホテル京都(京都府)
  • Year and Date: 2009-11-11
• [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] 海洋産天然物ブレベナールの全合成(招待講演) (2009)
  • Author(s): 門田功
  • Organizer: 2009年日本化学会西日本大会
  • Place of Presentation: 愛媛大学城北キャンパス(愛媛県)
  • Year and Date: 2009-11-07
• [Presentation] シンビオジノライドC14-C24およびC33-C42フラグメントの立体選択的合成 (2009)
  • Author(s): 角永悠一郎
  • Organizer: 2009年日本化学会西日本大会
  • Place of Presentation: 愛媛大学城北キャンパス(愛媛県)
  • 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: 第51回天然有機化合物討論会
  • Place of Presentation: 名古屋市公会堂(愛知県)
  • 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] シガトキシンCTX3CのEFGH環部の合成研究 (2009)
  • Author(s): 佐藤優樹
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 船橋
  • Year and Date: 2009-03-29
• [Presentation] シンビオジノライドC23-C34フラグメントの合成 (2009)
  • Author(s): 佐野将之
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 船橋
  • Year and Date: 2009-03-28
• [Presentation] シンビオジノライドC33-C42フラグメントの合成および構造決定 (2009)
  • Author(s): 角永悠一郎
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 船橋
  • Year and Date: 2009-03-28
• [Presentation] シンビオジノライドC79-C96フラグメントの立体選択的合成 (2009)
  • Author(s): 阿部享史
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 船橋
  • Year and Date: 2009-03-28
• [Presentation] 超炭素鎖有機分子シンビオジノライドの合成研究 (2008)
  • Author(s): 高村浩由
  • Organizer: 日本化学会西日本大会
  • Place of Presentation: 長崎
  • Year and Date: 2008-11-15
• [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
• [Presentation] ブレベナールの合成研究 (2008)
  • Author(s): 菊池重俊
  • Organizer: 日本化学会第88春季年会
  • Place of Presentation: 立教大学池袋キャンパス
  • Year and Date: 2008-03-27
• [Presentation] シガトキシンAB環部の立体選択的合成 (2008)
  • Author(s): 阿部享史
  • Organizer: 日本化学会第88春季年会
  • Place of Presentation: 立教大学池袋キャンパス
  • Year and Date: 2008-03-27
• [Presentation] シガトキシンCTX3CのA-E環部の合成研究 (2008)
  • Author(s): 宇仁巳由紀
  • Organizer: 日本化学会第88春季年会
  • Place of Presentation: 立教大学池袋キャンパス
  • Year and Date: 2008-03-27
• [Presentation] シンビオジノライドの合成研究(1) (2008)
  • Author(s): 村田健史
  • Organizer: 日本化学会第88春季年会
  • Place of Presentation: 立教大学池袋キャンパス
  • Year and Date: 2008-03-27
• [Presentation] シンビオジノライドの合成研究(2) (2008)
  • Author(s): 佐野将之
  • Organizer: 日本化学会第88春季年会
  • Place of Presentation: 立教大学池袋キャンパス
  • Year and Date: 2008-03-27
• [Remarks]
  • URL: http://chem.okayama-u.ac.jp/~organic/homejpn.html