2007 Fiscal Year Final Research Report Summary
Systematic Synthetic Stuchies on Bioactive Alkaloids and Their Biokeical Activiiies
| Project/Area Number |
18580104
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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 |
Bioproduction chemistry/Bioorganic chemistry
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| Research Institution | Shinshu University |
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Principal Investigator |
MAKABE Hidefumi Shinshu University, Graduate Scholl of Agriculture, Associate Professor (90313840)
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| Project Period (FY) |
2006 – 2007
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| Keywords | organic chemistry / synthetic chemistry / biological activity |
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| Research Abstract |
A number of alkaloids have been burl abundantly in nature and marry of than show interesting pharmalogical adivitites. Due to the amount of elk: slide is limited from the native, it is very important to prepare these compounds in order to study their binlogical properties. The aim of this study is to construct these compounds systenatically and solve the mechanism of action.
1. Synthetic studies on spectamine A
Recentlty spectiamine A was isolated by Ramo and m-workers at Shinshu Univemity icon African legume, (Is s i a apectahilis and identified as °Obenzoyl derivative of (+)-iso6-cassine. The key reaction of the synthesis of spectamine A is Pd-catayzed stereceelective cyclization to afford 2,6-traos-piperidine ring. When Pd.^2(dba)^3 was used as a catalyst and Cbm was used as a protecting group, the ratio of trail/cis was 79/21. The total synthesis of spectamine A is currently under way.
2. Synthess of pyranicyn
Total synthesis of pyranicin was achieved using C12Pd(CH3CN)2-catalyzed diastereoselective cyclization of the allyfic ester as the key step. The inhibitory activity of this compound for mitochiondrial NADH-uhiquioone oxidoreductase (complex I) was slightly poorer than that of ordinary mono-THF acetogenins such as cis-solamin. In the course of this study synthesis and determination of the absolute configuration of tookinelin was aka achieved.
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[Journal Article] Synthesis of Pyranicin and Its Inhibitory Action with Bovine Heart Mitochondria Complex I2008
Author(s)
Hattori, Y., Furuhata, S., Okajima, M., Konno, H., Abe, M., Miyoshi, H., Goto, T., Makabe, H
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Journal Title
Organic Letters 10
Pages: 717-720
Description
「研究成果報告書概要(欧文)」より
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[Journal Article] Synthesis, determination of the absolute configuration of tonkinelin, and inhibitory action with bovine heart mitochondrial complex I2007
Author(s)
Hattori, Y., Konno, H., Abe, M., Miyoshi, H., Goto, T., Makabe, H
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Journal Title
Bioorganic & Medicinal Chemistry 15
Pages: 3026-3031
Description
「研究成果報告書概要(欧文)」より
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[Presentation] Synthesis of pyranicin and its inhibitory action of mitochondrial complex I2008
Author(s)
Furuhata, S., Hattori, Y., Konno, H., Abe, M., Miyoshi, It ; Goto, T., Makabe, H
Organizer
Annual Meeting of JSBBA 2008
Place of Presentation
Nagoya, Japan
Year and Date
2008-03-22
Description
「研究成果報告書概要(欧文)」より
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[Presentation] Synthesis of annonaceous acetogenin, pyranicin2007
Author(s)
Furuhata, S., Hattori, Y., Goto, T., Makabe, Goto, T., Makabe, H
Organizer
147th Chubu Region Meeting of JSBBA
Place of Presentation
Nagoya, Japan
Year and Date
2007-10-21
Description
「研究成果報告書概要(欧文)」より
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[Presentation] Synthetic studies on pyranicin2007
Author(s)
Furuhata, S., Hattori, Y., Konno, H., Goto, T., Makabe, H
Organizer
Kansai-Tyubu Unified Meeting of JSBBA 2007
Place of Presentation
Nagoya, Japan
Year and Date
2007-09-22
Description
「研究成果報告書概要(欧文)」より
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[Presentation] Synthesis of Pyranicin via Pd(111) Catalyzed Diastereoselective Cyclization2007
Author(s)
Hattori, Y., Furuhata, S., OKajima, M., Konno, IL, Goto, T., Makabe, H
Organizer
14th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
Place of Presentation
Nara, Japan
Year and Date
2007-08-03
Description
「研究成果報告書概要(欧文)」より
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[Presentation] Synthesis of annonaceous acetogenin, pyranicin2007
Author(s)
Furuhata, S., Hattori, Y., Goto, T., Makabe, Goto, T., Makabe, H
Organizer
Annual Meeting of JSBBA 2008
Place of Presentation
Tokyo, Japan
Year and Date
2007-03-25
Description
「研究成果報告書概要(欧文)」より
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[Presentation] Synthetic studies on 2,6-disubstituted piperidine alkaroids, (-)-cassine and spectamine A and annonaceous acetogenin, pyranicin via palladium catalyzed six-membered ring formation2006
Author(s)
Hattori, Y., Furuhata, S., Matsumoto, W., Kong, L. K., Konno, IL, Kamo, T., Hirota, M., Goto, T., Makabe, H
Organizer
48th Symposium on the Chemistry of Natural Products
Place of Presentation
Sendai, Japan
Year and Date
20061011-13
Description
「研究成果報告書概要(欧文)」より
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