2004 Fiscal Year Final Research Report Summary
Phenolic oxidation towards synthesis of bioactive cyclic peptides
| Project/Area Number |
15510181
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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 |
Living organism molecular science
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| Research Institution | Keio University |
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Principal Investigator |
NISHIYAMA Shigeru Keio University, Faculty of Science and Technology, Professor, 理工学部, 教授 (20137988)
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| Project Period (FY) |
2003 – 2004
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| Keywords | Phenolic oxidation / Electroorganic chemistry / Thallium(III) oxidation / Aeroplysinin-1 / Eurypamide / Calafianin / Verbenachalcone / Heliannuol |
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| Research Abstract |
Synthetic studies on bioactive substances including natural products by phenolic oxidation employing anodic and thallium (III) oxidation reactions as key steps, was undertaken in this research project, as follows. (1)Synthesis of eurypamides. A, B, and D was successfully accomplished by the cyclization at the diaryl ether moieties. This result attached with findings of mono-cyclic peptide carrying the inhibitory activity against MRSA. (2)Bromination of germacrene D by bromonium ion electrochemically generated, provide the new bicyclic products, structures of which were spectroscopically determined. (3)The tandem reaction involving anodic oxidation of phenol derivatives, followed by the Lewis acid arrangement, provides heliannuol E, an alleropathogenic substance of sunflower, along with its congeners. This investigation revealed that the selectivity of the arrangement reaction is conducted by stereochemistry and electric character of aromatic substituents. More effective biological activity than that of natural heliannuols, was observed among synthetic intermediates and related products. (4)The electrochemical construction of the spiroisoxazoline derivatives made it possible to synthesize aerhoplysinin-1 and calafianin, spiroisoxazoline-class marine natural products. In the former investigation, the new ring-opening of the isoxazoline to the cyanohydrin was established, and the revision of the reported structure was undertaken. (5)Verbenachalcone, an activator of the nerve-growing factor of plant origin, was successfully synthesized by anodic oxidation of phenol derivatives carrying mixed halogen-substituents, which provided a methoxy diaryl ether moiety.
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[Patent(Industrial Property Rights)] 植物成長阻害剤2003
Inventor(s)
西山 繁, 土居 史尚, 小神野 孝尚, 小原 大雅, 須貝 威, 長谷川 宏司, 繁森 英幸
Industrial Property Rights Holder
西山 繁, 土居 史尚, 小神野 孝尚, 小原 大雅, 須貝 威, 長谷川 宏司, 繁森 英幸
Industrial Property Number
特願2003-345896 特開2005-112739
Filing Date
2003-10-03
Acquisition Date
2005-04-28
Description
「研究成果報告書概要(和文)」より
