Exploring the Biomass-Derived Chemical Space Emerging from Natural Dihydrochalcones through the Single-Step Hemisynthesis of Antibacterial Balsacones

The preparation of bioactive molecules from biomass substrates is a relevant approach to replace fossil resources. The substitution patterns of natural products facilitate the access to polyfunctional molecules; yet, only few families of biosourced compounds have been valued in this way. Renewable d...

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Bibliographic Details
Published in:ACS sustainable chemistry & engineering 2020-04, Vol.8 (16), p.6194-6199
Main Authors: Alsarraf, Jérôme, Bilodeau, Jean-François, Legault, Jean, Simard, François, Pichette, André
Format: Article
Language:English
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Summary:The preparation of bioactive molecules from biomass substrates is a relevant approach to replace fossil resources. The substitution patterns of natural products facilitate the access to polyfunctional molecules; yet, only few families of biosourced compounds have been valued in this way. Renewable dihydrochalcones and cinnamyl alcohols were combined in an expedient hemisynthesis of balsacones A, B, and C. These potent antibacterial compounds were prepared following a single-step Brønsted acid-catalyzed metal-free and protective-group-free Friedel–Crafts alkylation protocol. Novel analogues were also readily accessible relying on the diversity of biosourced precursors.
ISSN:2168-0485
2168-0485
DOI:10.1021/acssuschemeng.0c01545