1986 Fiscal Year Final Research Report Summary
Asymmetric Synthesis of Heterocyclic Compounds
| Project/Area Number |
60571009
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Kobe Women's College of Pharmacy |
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Principal Investigator |
NAITO Takeaki Assistant Professor, Kobe Women's College of Pharmacy, 薬学部, 助教授 (00068339)
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| Co-Investigator(Kenkyū-buntansha) |
MIYATA Okiko Lecturer, Kobe Women's College of Pharmacy, 薬学部, 助手 (90102110)
KIGUCHI Toshiko Lecturer, Kobe Women's College of Pharmacy, 薬学部, 講師 (70068344)
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| Project Period (FY) |
1985 – 1986
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| Keywords | Asymmetric Synthesis / Heterocyclic Compounds / Enamides / Isoquinoline / Indole / Photocyclization / Alkaloids / エメチン |
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| Research Abstract |
A new and simple synthetic methodology for the optically active heterocyclic compounds was developed by the application of two types of chiral circumstances to the photocyclizations of the anilides and enamides which are known to proceed via a common intermediate having two functional groups, the enolate and iminium moieties.
1. Asymmetric synthesis of quinolones by photocyclization of anilides involving enantioselective protonation of enolate moiety When we used a chiral dibasic acid possessing a <C_2> axis such as di-p-toluoyltartaric acid during the course of irradiation of anilides, optically active quinolones were obtained as a result of enantioselective protonation to the intermediate in moderate chemical and optical yields.
2. Asymmetric synthesis of isoquinolines and related compounds by photocyclization of enamides involving enantioselective reduction of iminium moiety Irradiation of enamides in the presence of chiral metal hydride complex of lithium aluminum hydride-chiral amino-alcohol afforded the optically active 8-oxoberbines, thus completing the asymmetric synthesis of (-)-Xylopinine.
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