1993 Fiscal Year Final Research Report Summary
Synthetic Study of Naturally Occurring Indoles Possessing Various Substituents on Benzene Moiety.
| Project/Area Number |
03671017
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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 | TOHO UNIVERSITY |
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Principal Investigator |
MURAKAMI Yasuoki Toho University, Pharmaceutical Sciences, Professor, 薬学部, 教授 (20009179)
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| Co-Investigator(Kenkyū-buntansha) |
SUZUKI Hideharu Toho University, Pharmaceutical Sciences, Research Associate, 薬学部, 助手 (40187753)
WATANABE Toshiko Toho University, Pharmaceutical Sciences, Research Associate, 薬学部, 助手 (40120323)
TANI Masanobu Toho University, Pharmaceutical Sciences, Research Associate, 薬学部, 助手 (50057733)
YOKOYAMA Yuusaku Toho University, Pharmaceutical Sciences, Associate Professor, 薬学部, 助教授 (10095325)
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| Project Period (FY) |
1991 – 1993
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| Keywords | Pyrrole / Indole / Alkaloid / Regiospecific / Acylation / Bromination / Hymenin |
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| Research Abstract |
A new synthetic methodology of indole nucleus starting with ethyl pyrrole-2-carboxylate (1) and its application were examined as follows.
1. The C_4-acylation of 1 by Friedel-Crafts reaction was examined, and the scope and limitation were established (1 -> 2). On the basis of it, a new synthetic route for indoles possessing various substituents on benzene moiety was developed.
2. By applying the above method, the synthesis of 9-methoxybenz[f] indole (6) was successful, and naturally occurring eupolauramine (7) was synthesized from 6.
3. Regioselectivity was found in the bromination of a methoxyindole derived from 1, and thus the regioselective bromination was systematically carried out on various methoxyindoles.
4. A synthesis of naturally occurring hymenin (11) from marine sponge was examined, and we have obtained the intermediate compound 14 at the present time.
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