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

  1. Takashi Nishiyama,
  2. Erina Hamada,
  3. Daishi Ishii,
  4. Yuuto Kihara,
  5. Nanase Choshi,
  6. Natsumi Nakanishi,
  7. Mari Murakami,
  8. Kimiko Taninaka,
  9. Noriyuki Hatae and
  10. Tominari ChoshiORCID Logo

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

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

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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

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