Synthetic studies of bioactive marine polycyclic ethers
| Project/Area Number |
15590028
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Meijo University |
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Principal Investigator |
MORI Yuji Meijo University, Faculty of Pharmacy, Professor, 薬学部, 教授 (40121511)
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| Project Period (FY) |
2003 – 2005
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| Project Status |
Completed (Fiscal Year 2005)
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| Budget Amount *help |
¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 2005: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 2004: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 2003: ¥1,500,000 (Direct Cost: ¥1,500,000)
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| Keywords | polycyclic ehter / synthesis / neurotoxin / gambierol / oxiranyl anion / diarrheic shellfish toxin / adrtiatoxin / ムール貝 / ラジカル反応 / テトラヒドロピラン / yessotoxin / ホタテガイ / adriatoxin / tetrahydropyan |
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| Research Abstract |
The marine polycyclic ether toxins, associated with the massive fish kills and human food poisoning from red tides and dinoflagellates have attracted much attention in the chemistry community for their intriguing molecular structure and biological activity. In this project, synthetic studies of adriatoxin and gambierol were undertaken, and the following results were obtained.
1.Synthetic studies of adriatoxin.
Adriatoxin, a diarrheic shellfish toxin isolated from mussels, consists of a decacyclic polyether framework containing three sulfate esters and a side chain. The ABCDEF ring system was synthesized in a convergent manner by coupling of the A and DEF rings which were prepared based on an oxiranyl anion strategy. On the other hand, the HIJ ring fragment was constructed by oxiranyl anion chemistry and radical cyclization.
2.Synthetic studies of gambierol.
Gambierol is a neurotoxin isolated from the ciguatera causative dinoflagellate Gambierdiscus toxicus. The structure consists of an octacyclic polyether containing three hydroxy groups and a partially skipped triene side chain. The ABCD ring system of gambierol has synthesized in 21 synthetic transformations starting from monocyclic D ring diol. The key reactions employed were alkylation of oxiranyl anion, 6-endo cyclization, dithiane-epoxide coupling reaction, and reductive etherification.
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Report
(4 results)
Research Products
(7 results)
