| 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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| Project Status |
Completed (Fiscal Year 2007)
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| Budget Amount *help |
¥3,390,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥390,000)
Fiscal Year 2007: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2006: ¥1,700,000 (Direct Cost: ¥1,700,000)
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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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