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Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine B

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...

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Autores principales: Nishiyama, Takashi, Hamada, Erina, Ishii, Daishi, Kihara, Yuuto, Choshi, Nanase, Nakanishi, Natsumi, Murakami, Mari, Taninaka, Kimiko, Hatae, Noriyuki, Choshi, Tominari
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7991618/
https://www.ncbi.nlm.nih.gov/pubmed/33796160
http://dx.doi.org/10.3762/bjoc.17.62
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author Nishiyama, Takashi
Hamada, Erina
Ishii, Daishi
Kihara, Yuuto
Choshi, Nanase
Nakanishi, Natsumi
Murakami, Mari
Taninaka, Kimiko
Hatae, Noriyuki
Choshi, Tominari
author_facet Nishiyama, Takashi
Hamada, Erina
Ishii, Daishi
Kihara, Yuuto
Choshi, Nanase
Nakanishi, Natsumi
Murakami, Mari
Taninaka, Kimiko
Hatae, Noriyuki
Choshi, Tominari
author_sort Nishiyama, Takashi
collection PubMed
description 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.
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spelling pubmed-79916182021-03-31 Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine B Nishiyama, Takashi Hamada, Erina Ishii, Daishi Kihara, Yuuto Choshi, Nanase Nakanishi, Natsumi Murakami, Mari Taninaka, Kimiko Hatae, Noriyuki Choshi, Tominari Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2021-03-16 /pmc/articles/PMC7991618/ /pubmed/33796160 http://dx.doi.org/10.3762/bjoc.17.62 Text en Copyright © 2021, Nishiyama et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/terms/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the author(s) and source are credited and that individual graphics may be subject to special legal provisions. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms/terms)
spellingShingle Full Research Paper
Nishiyama, Takashi
Hamada, Erina
Ishii, Daishi
Kihara, Yuuto
Choshi, Nanase
Nakanishi, Natsumi
Murakami, Mari
Taninaka, Kimiko
Hatae, Noriyuki
Choshi, Tominari
Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine B
title Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine B
title_full Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine B
title_fullStr Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine B
title_full_unstemmed Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine B
title_short Total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine B
title_sort total synthesis of pyrrolo[2,3-c]quinoline alkaloid: trigonoine b
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7991618/
https://www.ncbi.nlm.nih.gov/pubmed/33796160
http://dx.doi.org/10.3762/bjoc.17.62
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