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Article

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Accepted version

Publication date

2024-07-19

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/222728

Synthesis of the ABC Core of Daphniphyllum Alkaloids with a [5-6-7] Azatricyclic Scaffold via Ring Expansion of Azabicyclic and Azatricyclic Building Blocks

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https://doi.org/10.1021/acs.joc.4c01090

Abstract

The [5–6–7] azatricyclic ABC core, found in several Daphniphyllum alkaloids, has been synthesized through a novel route involving ring expansion of a perhydroindolone to afford the AC ring system and a radical B ring closure as key steps. The level of functionalization of the reported octahydro-1,7-ethanocyclohepta[b]pyrroles suggests that they can serve as valuable building blocks in this alkaloid field. Also reported is the first synthesis of homomorphans by the ring enlargement of 2-azabicyclo[3.3.1]nonanes.

Subject

Mescles, Compostos orgànics, Cetones

Subject (English)

Mixtures, Organic compounds, Ketones

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Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)

Citation

MARQUÈS, Clàudia, et al. Synthesis of the ABC Core of Daphniphyllum Alkaloids with a [5-6-7] Azatricyclic Scaffold via Ring Expansion of Azabicyclic and Azatricyclic Building Blocks. Journal of Organic Chemistry. 2024. Vol. 89, num. 14, pags. 10212-10222. ISSN 0022-3263. [consulted: 9 of June of 2026]. Available at: https://hdl.handle.net/2445/222728

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