A concise asymmetric synthesis of torcetrapib

M Guinó, PH Phua, JC Caille, KK Hii

Index: Guino, Meritxell; Pim, Huat Phua; Caille, Jean-Claude; King, Kuok Hii Journal of Organic Chemistry, 2007 , vol. 72, # 16 p. 6290 - 6293

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Citation Number: 24

Abstract

Preparative routes for compound 1 were first disclosed by its inventors in the patent literature 6 and subsequently in two journal articles. 7 In one of these reports, the tetrahydroquinoline ring was constructed by a stereospecific ring cyclization of an acyl immonium ion, generated from the N-arylated amino acid derivative 2a (Scheme 1). Asymmetric synthesis of this key intermediate was achieved in seven steps from (R)-2-aminobutanol, involving the use of protecting ...