Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine B
| Autor: | Mari Murakami, Daishi Ishii, Erina Hamada, Tominari Choshi, Nanase Choshi, Yuuto Kihara, Noriyuki Hatae, Takashi Nishiyama, Kimiko Taninaka, Natsumi Nakanishi |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
2-azahexatiriene system
electrocyclization 010405 organic chemistry Stereochemistry carbodiimide Alkaloid Organic Chemistry Quinoline Total synthesis 010402 general chemistry 01 natural sciences 0104 chemical sciences lcsh:QD241-441 chemistry.chemical_compound trigonoine b chemistry lcsh:Organic chemistry Yield (chemistry) pyrrolo[2 3-c]quinoline Moiety lcsh:Q Benzene lcsh:Science Carbodiimide |
| Zdroj: | Beilstein Journal of Organic Chemistry, Vol 17, Iss 1, Pp 730-736 (2021) |
| ISSN: | 1860-5397 |
| Popis: | The first total synthesis of the pyrrolo[2,3-c]quinoline alkaloid trigonoine B (1) was accomplished via a six-step sequence involving the construction of an N-substituted 4-aminopyrrolo[2,3-c]quinoline framework via electrocyclization of 2-(pyrrol-3-yl)benzene containing a carbodiimide moiety as a 2-azahexatriene system. The employed six-step sequence afforded trigonoine B (1) in 9.2% overall yield. The described route could be employed for the preparation of various N-substituted 4-aminopyrroloquinolines with various biological activities. |
| Databáze: | OpenAIRE |
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