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Published on: August 14, 2019
Asymmetric Total Synthesis of Fleminchalcone C: A Tyrosinase Inhibitor from Flemingia philippinensis
Nanling Liu1, Fulian Tang1, Zhi-Feng Teng1
1School of Life Science and Engineering, Southwest Jiaotong University, Chengdu610031, People's Republic of China.
Abstract:
Fleminchalcone C is a prenylated dihydrochalcone isolated from Flemingia philippinensis featuring a chiral benzodihydrofuran core and shows promise for the treatment of hyperpigmentation disorders. Herein, we report the first asymmetric total synthesis of both enantiomers of fleminchalcone C. A concise nine-step sequence from known prenylated phenol 6 was developed, highlighted by asymmetric epoxidation to establish the key chiral center. This synthetic access enabled definitive assignment of the absolute configuration and revealed a pronounced stereochemical dependence on tyrosinase inhibitory activity.

