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- W2090290216 abstract "Amide of an octanoic acid possessing an aryl group at C3 position is a highly potent ACAT inhibitor. In this paper, we describe a synthetic access to this class of compounds as optically active forms. The key reaction is substitution of the allylic picolinate of (S,Z)-8-(benzyloxy)oct-5-en-4-ol with a copper reagent derived from (benzo[d][1,3]dioxol-4-yl)MgBr and CuBr·Me2S to produce anti SN2′ product regio- and stereo-selectively. The product was hydrogenated to afford (S)-3-benzo[d][1,3]dioxol-4-yloctan-1-ol, which upon oxidation furnished the octanoic acid. Finally, the acid was converted with 2,6-(i-Pr)2C6H3NH2 to the target amide via acid chloride. In a similar way, the one-carbon long homolog was synthesized." @default.
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- W2090290216 date "2010-11-01" @default.
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- W2090290216 title "Synthesis of ACAT inhibitors through substitution using allylic picolinate and copper reagent" @default.
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- W2090290216 doi "https://doi.org/10.1016/j.tetlet.2010.09.035" @default.
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