Antioxidants have potential for the treatment of stroke and neurodegeneration, and chimeric compounds that combine a flavon-3-ol head group related to myricetin and a lipophilic decyl tail are known to protect membranes from oxidative damage at least as well as vitamin E. New flavon-3-ols that are highly hydroxylated in the B ring in ways not found in natural flavon-3-ols and bearing a lipophilic decyl tail have been prepared from trimethoxy-and tetramethoxybenzoic acids accessed by lithiation-carboxylation reactions. Direct enolate acylation was preferred over Baker-Venkataraman rearrangement when there were methoxy groups at both the 2-and the 6-position of the benzoic acid derivatives.
Caldwell, S. T., Hartley, R. C., McPhail, D. B., & Duthie, G. G. (2012). Synthesis of polyhydroxylated flavonoids bearing a lipophilic decyl tail as potential therapeutic antioxidants. Canadian Journal of Chemistry, 90(1), 23-33. https://doi.org/10.1139/v11-087