Site-Divergent C-H Bond Functionalization of Free Phenols Enables Hydroxyflavanones
Jia Xu1, Li-Xin Zhang2, Xiao-Yu Yang1
1College of Pharmacy, National & Local Joint Engineering Research Center of Targeted and Innovative Therapeutics, Chongqing Key Laboratory of Kinase Modulators as Innovative Medicine, Chongqing University of Arts and Sciences, Chongqing 402160, China.
None:
A solvent-controlled strategy to regulate the site-selectivity of free phenols and stereospecificity of 1,4-addition is presented, thereby divergently producing 4'-hydroxyflavanone and 2'-hydroxyflavanone via site-specific C-H bond functionalization. This protocol is applicable to a diverse range of free phenols. Furthermore, this strategy efficiently accesses natural product-like frameworks, including Eriodictyol, Narigenin, (+)-Anastatins A, (+)-Anastatins B, and (+)-Cycloaltilisin 7 with high selectivity. Late-stage modifications of pharmaceuticals, such as Ethinylestradiol, β-Estradiol, Ezetimibe, and Estrone, are certainly enabling. Importantly, the IC50 values of the newly synthesized compounds 4o and 5m were determined to be in the submicromolar range, indicating a notably potent inhibitory effect. This finding for the synthesis of hydroxyflavanones marks a significant stride in overcoming the extraction challenges of natural products.
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