2010 Fiscal Year Final Research Report
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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| Keywords | 合成化学 |
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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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[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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