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Efficient Synthesis of Frutinone A and Its Derivatives through Palladium‐Catalyzed CH Activation/Carbonylation
Author(s) -
Shin Yongje,
Yoo Changho,
Moon Youngtaek,
Lee Yunho,
Hong Sungwoo
Publication year - 2015
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201402876
Subject(s) - carbonylation , palladium , catalysis , chemistry , organic chemistry , carbon monoxide
Frutinone A, a biologically active ingredient of an antimicrobial herbal extract, demonstrates potent inhibitory activity towards the CYP1A2 enzyme. A three‐step total synthesis of frutinone A with an overall yield of 44 % is presented. The construction of the chromone‐annelated coumarin core was achieved through palladium‐catalyzed CH carbonylation of 2‐phenolchromones. The straightforward synthetic route allowed facile substitutions around the frutinone A core and thus rapid exploration of the structure–activity relationship (SAR) profile of the derivatives. The inhibitory activity of the synthesized frutinone A derivatives were determined for CYP1A2, and ten compounds exhibited one‐to‐two digit nanomolar inhibitory activity towards the CYP1A2 enzyme.