A Facile Synthetic Approach to Prenylated Flavanones: First Total Syntheses of (±)-Bonannione A and (±)-Sophoraflavanone A
2001
A facile and efficient approach for the syntheses of both C-8 and C-6 prenylated flavonoids has been developed that features a highly regioselective prenylation of 2,4,6-trihydroxyacetophenone and regioselective cyclization of prenylated polyhydroxy chalcones. Thus, the first efficient total syntheses of (±)-sophoraflavanone A (1) and (±)-bonannione A (2), two naturally occurring geranylated flavanones with antibacterial activities, have been achieved starting from the key intermediate 3 via regioselective cyclization of geranylated tetrahydroxychalcone 4.
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