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- W4225262841 endingPage "2022" @default.
- W4225262841 startingPage "2011" @default.
- W4225262841 abstract "The stereodivergent total synthesis of all stereoisomers of bioactive natural compounds to enable complete evaluation of stereochemical structure-activity relationships is highly challenging and valuable. Naturally occurring flavaglines, containing a compact functionalized cyclopenta[b]benzofuran scaffold, display a wide range of biological activities. Herein, we disclose a novel stereodivergent allylic alkylation of benzofuran-3(2H)-one that relies on the synergistic catalysis of a chiral N,N′-dioxide-Co(or Ni) complex and a phosphoramidite-Ir catalyst. All four possible stereoisomers of the α-allylated product are provided with excellent diastereo- and enantioselectivities by appropriate permutations of the two chiral catalysts. The concise synthesis of the targeted molecule rocaglaol is furnished in a stereodivergent manner, following a uniform synthetic route and using the same set of starting materials. Subsequently, a preliminary study on the anticancer activity for eight stereoisomers of rocaglaol reveals the pronounced influence of stereochemistry variations on biological activity." @default.
- W4225262841 created "2022-05-04" @default.
- W4225262841 creator A5000050521 @default.
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- W4225262841 creator A5062915218 @default.
- W4225262841 creator A5072091290 @default.
- W4225262841 creator A5077217676 @default.
- W4225262841 date "2022-07-01" @default.
- W4225262841 modified "2023-10-16" @default.
- W4225262841 title "Stereodivergent total synthesis of rocaglaol initiated by synergistic dual-metal-catalyzed asymmetric allylation of benzofuran-3(2H)-one" @default.
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- W4225262841 doi "https://doi.org/10.1016/j.chempr.2022.04.006" @default.
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