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

Abstract : 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.
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Submitted on : Tuesday, May 21, 2019 - 9:39:18 PM
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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, American Chemical Society, 2018, 20 (23), pp.7424-7428. ⟨10.1021/acs.orglett.8b03148⟩. ⟨pasteur-02136204⟩

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