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

Alexis St-Gelais (1) , Jérôme Alsarraf (1) , Jean Legault (1) , Charles Gauthier (2, 1) , André Pichette (1)

1 UQAC - Université du Québec à Chicoutimi
2 INRS-IAF - Institut Armand Frappier

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.

Domains: Life Sciences [q-bio]

Alexis St-Gelais, Jérôme Alsarraf, Jean Legault, Charles Gauthier, André Pichette. Soft-enolization Baker–Venkataraman Rearrangement Enabled Total Synthesis of Dirchromones and Related 2-Substituted Chromones. Organic Letters, 2018, 20 (23), pp.7424-7428. ⟨10.1021/acs.orglett.8b03148⟩. ⟨pasteur-02136204⟩