کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5276316 | 1385554 | 2010 | 4 صفحه PDF | دانلود رایگان |
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 SN2Ⲡproduct 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.
The method is demonstrated by synthesis of two amides (n = 1, 2).
Journal: Tetrahedron Letters - Volume 51, Issue 46, 17 November 2010, Pages 6018-6021