Design of Solid Supported Metal Catalyst and The Application to Synthesis of Thallusin Analogues
| Project/Area Number |
20790025
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Tokushima Bunri University |
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Principal Investigator |
HIROFUMI Yamamoto Tokushima Bunri University, 薬学部, 助教 (70461366)
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| Project Period (FY) |
2008 – 2010
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| Project Status |
Completed (Fiscal Year 2010)
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| Budget Amount *help |
¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2010: ¥650,000 (Direct Cost: ¥500,000、Indirect Cost: ¥150,000)
Fiscal Year 2009: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2008: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
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| Keywords | 合成化学 / サルーシン / ノルサルーシン / ジピコリン酸 / 葉状体形成誘導活性 / 固相担持性触媒 / 炭素-窒素結合形成反応 / スルファメート / 辻-Trost型アリルアミノ化反応 / 固相担持性性水銀触媒 / 藻類成長促進因子 / タルーシン / タンデム環化反応 / 赤潮 / 緑潮 / グリーンタイド / 大型緑藻類 / 固相担持性水銀触媒 / シラフェニル水銀トリフラート / マイクロウェーブ / 触媒 / フロー反応 / 触媒環化反応 / 葉状態形成誘導活性 |
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| Research Abstract |
We developed a procedure to generate the first solid supported mercuric salt, silaphenylmercuric triflate, by heating SiliaBond^[○!R] Phenyl (silica gel with phenyl group on its surface) with Hg(OAc)_2 in AcOH to 140℃ using microwave radiation following treatment with TfOH. This solid supported mercuric triflate showed remarkable catalytic activity for a indole synthesis, furanoyne cyclization, arylyne cyclization, tandem carbocyclization, and allylic amination. Because the SiliaBond^[○!R] Phenyl is a silica gel used for column chromatography, we established a highly efficient flow-reaction system useful for indole synthesis and arylyne cyclization by simply charging the immobilized catalyst in a small glass tube. Moreover, catalytic tandem carbocyclization of homofarnesic acid using the solid catalyst was utilized for the total synthesis of (±)-thallusin and analogues were undertaken to allow a detailed examination of thallusin's faliaceous morphology-inducing activity.
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Report
(4 results)
Research Products
(27 results)
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[Journal Article] Synthesis and evaluation of novel phosphate ester analogs as neutral sphingomyelinase inhibitors.2010
Author(s)
H.Imagawa, M.Oda, T.Takemoto, R.Yamauchi, T.Yoshikawa, H.Yamamoto, M.Nishizawa, H.Takahashi, M.Hashimoto, K.Yabiku, M.Nagahama, J.Sakurai
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Journal Title
Bioorg.Med.Chem.Lett. 20
Pages: 3868-3871
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[Presentation] サルーシン及びその類縁体の効率的合成2010
Author(s)
高木悠一, 光山忠史, 山本博文, 今川洋, 西沢麦夫, 兼目裕充, 志津里芳一, 松尾嘉英
Organizer
第52回天然有機化合物討論会
Place of Presentation
静岡コンベンションアーツセンター(静岡)
Year and Date
2010-09-29
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[Presentation] サルーシン及び類縁体の合成2009
Author(s)
光山忠史, 高木悠一, 山本博文, 今川洋, 西沢麦夫, 志津里芳一, 松尾嘉英
Organizer
第35回反応と合成の進歩シンポジウム
Place of Presentation
金沢市文化ホール(石川県)
Year and Date
2009-11-16
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