2003 Fiscal Year Final Research Report Summary
Asymmetric synthesis of bioactive azapyranose derivatives
| Project/Area Number |
14540491
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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 |
Organic chemistry
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| Research Institution | Shizuoka University |
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Principal Investigator |
TAKABE Kunihiko Shizuoka University, Faculty of Engineering, Professor, 工学部, 教授 (30022239)
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| Co-Investigator(Kenkyū-buntansha) |
MASE Nobuyuki Shizuoka University, Faculty of Engineering, Associate Professor, 工学部, 助手 (40313936)
YODA Hidemi Shizuoka University, Faculty of Engineering, Associate Professor, 工学部, 助教授 (20201072)
WATANABE Naoharu Shizuoka University, Faculty of Agriculture, Professor, 農学部, 教授 (90230979)
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| Project Period (FY) |
2002 – 2003
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| Keywords | Azasugar / Enzymatic asymmetric induction / Enzyme inhibition / Alkaloid / Pharmacological activity / Azapyranose |
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| Research Abstract |
Azasugar derivatives have been anticipated to be new designed pharmaceuticals which are related to the inhibition of glycosidase.
1.Syntheses of isofagomine and paroxetine were investigated. These azasugars potentially have anti-HIV and anti-Alzheimer activities and could be prepared from N-Boc-γ-benzyloxymethyl-α,β-unsaturated-δ-lactam 1, which was produced by chemo-enzymatic process. We achieved the synthesis of isofagomine, however unfortunately, the diastereoselectivity in dihydroxylation of 1 was low. On the other hand, Michael addition of p-fluorophenyl-Grignard reagent to 1 showed high diastereoselectivity and chemical yield. Transformations of Michael adduct gave the chiral paroxetine in good yield.
2.Recently we reported the synthesis of a chiral γ-acetoxy-α,β-unsaturated-γ-lactam 2, which was an important chiral building block. The synthesis of (-)-2-epilentiginosine using the chiral lactam 2 was examined. Dihydroxylation of 2, then allylation smoothly proceeded. Transformations of allylation-product gave (-)-2-epilentiginosine, its spectral data was identical with authentic data.
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Research Products
(10 results)
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[Publications] Bessho, J.-i., Shimotsu, Y., Mizumoto, S., Mase, N., Yoda, H., Takabe, K.: "Convenient synthesis of pulchellalactam, a CD45 protein tyrosine phosphatase inhibitor from the marine fungus Corollospora pulchella, and its related compounds."Heterocycles. 63(5). 1013-1016 (2004)
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「研究成果報告書概要(欧文)」より
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[Publications] Takabe, K., Hashimoto, H., Sugimoto, H., Nomoto, M., Yoda, H.: "First asymmetric synthesis of the marine furanosesterterpene natural product, (18S)-variabilin employing enzymatic desymmetrization of propanediol derivatives"Tetrahedron : Asymmetry. 15(6). 909-919 (2004)
Description
「研究成果報告書概要(欧文)」より
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