posted on 2022-11-17, 14:55authored byDaniela Fregoso-López, Luis D. Miranda
The first synthetic strategy for nonsymmetrical 3,3″-biflavones
is described. To this end, a novel visible-light iridium-catalyzed
radical C-3 alkylation of flavones with o-methoxy
phenacyl bromides was developed. Selective demethylation of the alkylated
flavones and acylation through a Baker–Venkataraman rearrangement
with diverse acyl chlorides afforded a library of 20 structurally
novel biflavones. This modular strategy rapidly expands the structural
complexity and diversity of these privileged scaffolds.