A facile synthetic approach to prenylated flavanones: first total syntheses of (+/-)-bonannione A and (+/-)-sophoraflavanone A.
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.
Wang
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Y
National Laboratory of Applied Organic Chemistry & Institute of Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, People's Republic of China.
Tan
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W
Li
W Z
WZ
Li
Y
Y
D000890:Anti-Infective Agents / Q000138:chemical synthesis*; D044950:Flavanones; D005419:Flavonoids / Q000138:chemical synthesis*; D008956:Models, Chemical
D000890:Anti-Infective Agents; D044950:Flavanones; D005419:Flavonoids; C433577:bonannione A; C433578:sophoraflavanone A