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

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

Alexis St-Gelais ¹ Jérôme Alsarraf ¹ Jean Legault ¹ Charles Gauthier ^{2, 1} André Pichette ^{1, *}

* Corresponding author

1 UQAC - Université du Québec à Chicoutimi

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.

Document type :

Journal articles

Domain :

Life Sciences [q-bio]

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https://hal-riip.archives-ouvertes.fr/pasteur-02136204
Contributor : Michel Courcelles <>
Submitted on : Tuesday, May 21, 2019 - 9:39:18 PM
Last modification on : Wednesday, August 14, 2019 - 2:10:02 PM

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

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

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