Beilstein J. Org. Chem.2019,15, 2958–2965, doi:10.3762/bjoc.15.291
biologically interesting chromone skeleton was realized by PhIO-mediated dehydrogenation of chromanones under mild conditions. Interestingly, this method also found application in the synthesis of the naturally occurring frutinoneA.
Keywords: chromanone; chromone; dehydrogenation; frutinoneA; PhIO
of the obtained chromone derivatives was their conversion to chromone-derived natural products. FrutinoneA, isolated from the leaves and root bark of Polygala fruticosa, shows various biological activities, including antibacterial, antioxidant, and potent cytochrome P450 1A2 inhibition (CYP1A2, IC50
= 5.3 nM) properties [90][91][92]. Treating the obtained chromene-3-carboxylate 2l with LiOH [93] led to the formation of the chromene-3-carboxylic acid G. Heating compound G overnight in the presence of AgNO3 and K2S2O8 afforded frutinoneA in an isolated yield of 45% (Scheme 5).
Conclusion
In summary
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Graphical Abstract
Figure 1:
Biologically active chromone derivatives.