| Project/Area Number |
14540500
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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 | Kagoshima University |
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Principal Investigator |
NAKATANI Munehiro Kagoshima University, Faculty of Science, Professor, 理学部, 教授 (30041221)
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| Co-Investigator(Kenkyū-buntansha) |
OKAMURA Hiroaki Kagoshima University, Faculty of Science, Associate professor, 理学部, 助教授 (30244221)
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| Project Period (FY) |
2002 – 2003
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| Project Status |
Completed (Fiscal Year 2003)
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| Budget Amount *help |
¥2,300,000 (Direct Cost: ¥2,300,000)
Fiscal Year 2003: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 2002: ¥2,000,000 (Direct Cost: ¥2,000,000)
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| Keywords | Aminocyclitols / Base-catalyzed asymmetric Diels-Alder reaction / (±)-Varidamine / (±)-2-Epivaridamine / (+)-Epiepoformin / (-)-phyllostine / Diels-Alder反応 / 全合成 / N-Tosyl-3-hydroxy-2-pyridone / (±)-Validamine / (±)-2-Epivalidamine |
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| Research Abstract |
This project was carried out by two subgroups.
Subgroup 1 examined a diastereoselective base-catalyzed Diels-Alder (DA) reaction With several optically active dienophiles, and found that the reaction gave desired product up to 91 %de by using (+)-dienophile and cinchonidine as an optically active amine catalyst. This reaction was suitable for the starting material of the asymmetric synthesis of titled compounds.
Subgroup 2 first studied the synthesis of racemic aminocyclitols using readily obtained racemic starting material, and established the afficient synthetic route toward validamine and 2-epivalidamine via a common intermediate.
On the other hand, an asymmetric total synthesis of naturally occurring cyclohexeneoxides, (+)-epiepoformin and (-)-phyllostine, has been also achieved using the chiral building block available from our base-catalyzed DA reaction of 3-hydroxy-2-pyrone in this study period.
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