Total Synthesis of Pyrrolo[2,3-c]quinoline Alkaloid: Trigonoine B

Takashi Nishiyama; Erina Hamada; Daishi Ishii; Yuuto Kihara; Nanase Choshi; Natsumi Nakanishi; Mari Murakami; Kimiko Taninaka; Noriyuki Hatae; Tominari Choshi

doi:10.3762/bxiv.2021.6.v1

Total Synthesis of Pyrrolo[2,3-c]quinoline Alkaloid: Trigonoine B

Takashi Nishiyama,
Erina Hamada,
Daishi Ishii,
Yuuto Kihara,
Nanase Choshi,
Natsumi Nakanishi,
Mari Murakami,
Kimiko Taninaka,
Noriyuki Hatae and
Tominari Choshi

Submitting author affiliation: Fukuyama University, Fukuyama, Japan

Beilstein Arch. 2021, 20216. https://doi.org/10.3762/bxiv.2021.6.v1

Published 26 Jan 2021

Preprint

This preprint has not been peer-reviewed. When a peer-reviewed version is available, this information will be updated.

Abstract

The first total synthesis of 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.

Keywords: pyrrolo[2,3-c]quinoline; trigonoine B; electrocyclization; 2-azahexatiriene system; carbodiimide

Supporting Information

Format: PDF

Size: 7.2 MB

Download

How to Cite

When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Nishiyama, T.; Hamada, E.; Ishii, D.; Kihara, Y.; Choshi, N.; Nakanishi, N.; Murakami, M.; Taninaka, K.; Hatae, N.; Choshi, T. Beilstein Arch. 2021, 20216. doi:10.3762/bxiv.2021.6.v1

Download Citation
Download RIS (Reference Manager)	Download BIB (BIBTEX)

Subject Areas

Show All Preprints Nanotechnology Organic chemistry

Bioorganic chemistry / chemical biology Catalysis Chemical methods and reactions Flow and process chemistry Green and sustainable chemistry Materials chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry

Subject Areas

Show All Preprints Nanotechnology Organic chemistry

aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)

Total Synthesis of Pyrrolo[2,3-c]quinoline Alkaloid: Trigonoine B

This preprint has not been peer-reviewed. When a peer-reviewed version is available, this information will be updated.

Abstract

Supporting Information

How to Cite

Subject Areas

Subject Areas

Other Beilstein-Institut Open Science Activities