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Soft-enolization Baker-Venkataraman Rearrangement Enabled Total Synthesis of Dirchromones and Related 2-Substituted Chromones.

St-Gelais, Alexis, Alsarraf, Jérôme, Legault, Jean, Gauthier, Charles ORCID: https://orcid.org/0000-0002-2475-2050 et Pichette, Andre (2018). Soft-enolization Baker-Venkataraman Rearrangement Enabled Total Synthesis of Dirchromones and Related 2-Substituted Chromones. Organic Letters , vol. 20 , nº 23. p. 7424-7428. DOI: 10.1021/acs.orglett.8b03148.

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Résumé

A seven-step total synthesis of the original scaffold of cytotoxic dirchromones involving an unprecedented soft-enolization Baker-Venkataraman rearrangement was designed. The methodology enabled access to naturally occurring dirchromone 1 (21% overall yield) at gram-scale, which was screened for cytotoxicity against 13 cancer cell lines. The scope of the soft-enolization Baker-Venkataraman rearrangement encompasses diversely substituted dirchromones, including flavonoids, 2-styrylchromones, and 2-phenylethylchromones.

Type de document: Article
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Centre: Centre INRS-Institut Armand Frappier
Date de dépôt: 20 nov. 2019 20:46
Dernière modification: 15 févr. 2022 17:29
URI: https://espace.inrs.ca/id/eprint/8179

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