Synthesis of a muscarinic receptor antagonist via a diastereoselective Michael reaction, selective deoxyfluorination and aromatic metal-halogen exchange reaction

…, J Lynch, P Maligres, A Molina, T Nemoto…

文献索引：Mase; Houpis; Akao; Dorziotis; Emerson; Hoang; Iida; Itoh; Kamei; Kato; Kawasaki; Lang; Lee; Lynch; Maligres; Molina; Nemoto; Okada; Reamer; Song; Tschaen; Wada; Zewge; Volante; Reider; Tomimoto Journal of Organic Chemistry, 2001 , vol. 66, # 20 p. 6775 - 6786

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被引用次数: 89

摘要

An efficient synthesis of a structurally unique, novel M3 antagonist 1 is described. Compound 1 is conveniently disconnected retrosynthetically at the amide bond to reveal the acid portion 2 and the amine fragment 3. The synthesis of key intermediate 2 is highlighted by a ZnCl2-MAEP complex 19 catalyzed diastereoselective Michael reaction of dioxolane 7 with 2-cyclopenten-1-one (5) to establish the contiguous quaternary-tertiary chiral centers ...