Synthesis of ACAT inhibitors through substitution using allylic picolinate and copper reagent

Y Kobayashi, P Lalitnorasate, Y Kaneko, Y Kiyotsuka…

Index: Kobayashi, Yuichi; Lalitnorasate, Paveena; Kaneko, Yuki; Kiyotsuka, Yohei; Endo, Yoshiki Tetrahedron Letters, 2010 , vol. 51, # 46 p. 6018 - 6021

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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 ...