Studies on strigols, signaling molecules of symbiotic associations with fungi and phytohormones inhibiting shoot branching

• Project/Area Number: 21710214
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Living organism molecular science
• Research Institution: Keio University
• Principal Investigator: SHOJI Mitsuru Keio University, 薬学部, 准教授 (30339139)
• Project Period (FY): 2009 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000); Fiscal Year 2010: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000); Fiscal Year 2009: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
• Keywords: 5-デオキシストリゴール / 全合成 / 菌根共生 / 植物ホルモン / 還元的炭素-炭素結合形成反応 / 生物有機化学 / 有機化学

Research Abstract

The total synthesis of 5-deoxystrigol was carried out via regioselective coupling reaction between the aluminum ate complex of an alkyne and an epoxide, and two reductive carbon-carbon bond formations in the presence of transition metals such as titanium and samarium as key steps. A lipase-mediated kinetic resolution was successfully proceeded to afford optically active 5-deoxystrigols.

Research Products

• [Journal Article] Total Synthesis of (±)-5-Deoxystrigol via Reductive Carbon-Carbon Bond Formation (2009)
  • Author(s): 庄司満、鈴木恵理子、上田実
  • Journal Title: The Journal of Organic Chemistry 74巻 Pages: 3966-3969
  • Peer Reviewed
• [Journal Article] Total Synthesis of (±)-5-Deoxystrigol via Reductive Carbon-Carbon Bond Formation (2009)
  • Author(s): 庄司満、鈴木恵理子、上田実
  • Journal Title: The Journal of Organic Chemistry 74 Pages: 3966-3669
  • Peer Reviewed
• [Presentation] 多環式生物活性天然物の全合成 (2011)
  • Author(s): 庄司満
  • Organizer: 日本薬学会第131年会一般シンポジウム 有機合成化学の若い力-創造への挑戦-
  • Place of Presentation: 静岡県静岡市
  • Year and Date: 2011-03-29
• [Presentation] 多環式生物活性天然物の全合成 (2011)
  • Author(s): 庄司満
  • Organizer: 日本薬学会第131会年会一般シンポジウム 有機合成化学の若い力-創造への挑戦-
  • Place of Presentation: 静岡県静岡市
  • Year and Date: 2011-03-29
• [Presentation] Total synthesis of (±)-5-deoxystrigol via reductive carbon-carbon bond formation (2010)
  • Author(s): 庄司満、鈴木恵理子、上田実
  • Organizer: 2010 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2010)
  • Place of Presentation: アメリカハワイ州ホノルル
  • Year and Date: 2010-12-19
• [Presentation] Total synthesis of (±)-5-deoxystrigol via reductive carbon-carbon bond for mation (2010)
  • Author(s): 庄司満、鈴木恵理子、上田実
  • Organizer: 2010 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2010)
  • Place of Presentation: アメリカハワイ州ホノルル
  • Year and Date: 2010-12-19
• [Presentation] Total Synthesis of (±)-5-Deoxystrigol via Reductive Carbon-Carbon Bond Formation (2009)
  • Author(s): 鈴木恵理子、庄司満、上田実
  • Organizer: The 5^<th> Japan-Korea Young Scientists Meeting on Bioorganic and Natural Products Chemistry
  • Place of Presentation: 静岡県熱海市
  • Year and Date: 2009-08-27
• [Presentation] 天然物合成と人 (2009)
  • Author(s): 庄司満
  • Organizer: 東北大学第1回GCOE有機系若手シンポジウム
  • Place of Presentation: 宮城県仙台市
  • Year and Date: 2009-08-01