A marine lethal toxin polycavernoside A: synthesis and exploration of the molecular mechanism of action

• Project/Area Number: 22603001
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: ケミカルバイオロジー
• Research Institution: Tohoku University
• Principal Investigator: KASAI Yusuke 東北大学, 大学院・生命科学研究科, 産学官連携研究員 (50379286)
• Project Period (FY): 2010 – 2012
• Project Status: Completed (Fiscal Year 2012)
• Budget Amount: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000); Fiscal Year 2012: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2011: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2010: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
• Keywords: 天然物化学 / 海産毒 / 有機合成 / 鈴木-宮浦反応 / マクロラクトン化 / ポリカバノシド / マクロリド配糖体

Research Abstract

A total synthesis of (-)-polycavernoside A, a marine lethal toxin isolated from the edible alga Gracilaria edulis, has been achieved via a convergent approach. The synthesis is highlighted by catalytic asymmetric syntheses of the two key fragments and their union through Suzuki-Miyaura coupling and Keck macrolactonization. Efficient synthesis of L-fucosyl-D-xylose part was developed by using armed-disarmed concept.

Research Products

• [Journal Article] Total Synthesis of (-)-Polycavernoside A: Suzuki-Miyaura Coupling Approach (2012)
  • Author(s): Yusuke Kasai, Takanori Ito, Makoto Sasaki
  • Journal Title: Org. Lett Volume: 14(12) Issue: 12 Pages: 3186-3189
  • DOI: 10.1021/ol301278e
  • Peer Reviewed
• [Journal Article] Strategies and Methods for the Total Synthesis of Ellagitanins (2012)
  • Author(s): Hidetoshi Yamada, Tsukasa Hirokane, Noriaki Asakura, Yusuke Kasai, Kohei Nagao
  • Journal Title: Current Organic Chemistry Volume: 16 Pages: 578-604
  • Peer Reviewed
• [Journal Article] Synthesis of 6-F-ergosterol and its influence on membrane-permeabilization of amphotericin B and Amphidinol 3 (2011)
  • Author(s): Yusuke, Kasai
  • Journal Title: Organic & Biomolecular Chemistry Volume: 9 Pages: 1437-1442
  • Peer Reviewed
• [Presentation] 海産毒ポリカバノシドAの全合成研究 (2012)
  • Author(s): 葛西祐介・伊藤崇則・佐々木誠
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 慶応義塾大学日吉キャンパス
  • Year and Date: 2012-03-28
• [Presentation] 海産毒ポリカバノシドAの全合成研究 (2012)
  • Author(s): 葛西祐介・伊藤崇則・佐々木誠
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 横浜
  • Year and Date: 2012-03-27
• [Presentation] 海産毒ポリカバノシドAの全合成研究 (2011)
  • Author(s): 葛西祐介・伊藤崇則・佐々木誠
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 横浜
  • Year and Date: 2011-03-26
• [Presentation] Synthetic Studies on Polycavernoside A (2010)
  • Author(s): Yusuke Kasai, Makoto Sasaki
  • Organizer: Pacifichem 2010
  • Place of Presentation: Hawaii, the United States
  • Year and Date: 2010-12-19
• [Presentation] Synthetic Studies on Polycavernoside A (2010)
  • Author(s): Yusuke Kasai, Makoto Sasaki
  • Organizer: Pacifichem2010
  • Place of Presentation: ホノルル、ハワイ,アメリカ
  • Year and Date: 2010-12-19
• [Presentation] 海産毒ポリカバノシドAの全合成研究 (2010)
  • Author(s): 葛西祐介・佐々木誠
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 大阪
  • Year and Date: 2010-03-28