1P17: o) Synthesis of novel flavonoids using aldol condensation a key step

C. J. Bennett et al.⁴⁹ prepared novel flavonoids that combine the radical-scavenging ability of myricetin with vitamin E’s ability to embed itself in membranes. Unlike myricetin, these potential therapeutic antioxidants effectively protect vitamin E-deficient microsomes from lipid peroxidation. The flavonoid head groups are prepared by aldol condensation followed by Algar–Flynn–Oyamada (AFO) oxidation or by Baker–Venkataraman rearrangement. The alkyl tails are introduced by Suzuki or Negishi palladium-catalysed cross-coupling or by crossmetathesis catalysed by first generation Grubbs catalyst. Aldol condensation with trimethoxybenzaldehyde (79) with 80 and 81 gave chalcones (76) and 77. Similarly 82, 83, 85 and 86 is prepared and further synthesized novel flavonoids using different step (Scheme 17).

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49. C. J. Bennett, S. T. Caldwell, D. B. McPhail, P. C. Morrice, G. G. Duthieb, and R. C. Hartleya, Bioorg.Med. Chem., 2004, 12, 2079
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