A practical synthesis of renin inhibitor MK-1597 (ACT-178882) via catalytic enantioselective hydrogenation and epimerization of piperidine intermediate

…, T Trinh, R Angelaud, PD O'Shea, S Abele…

文献索引：Molinaro, Carmela; Shultz, Scott; Roy, Amelie; Lau, Stephen; Trinh, Thao; Angelaud, Remy; O'Shea, Paul D.; Abele, Stefan; Cameron, Mark; Corley, Ed; Funel, Jacques-Alexis; Steinhuebel, Dietrich; Weisel, Mark; Krska, Shane Journal of Organic Chemistry, 2011 ,  vol. 76,  # 4  p. 1062 - 1071

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被引用次数: 16

摘要

A practical enantioselective synthesis of renin inhibitor MK-1597 (ACT-178882), a potential new treatment for hypertension, is described. The synthetic route provided MK-1597 in nine steps and 29% overall yield from commercially available p-cresol (7). The key features of this sequence include a catalytic asymmetric hydrogenation of a tetrasubstituted ene− ester, a highly efficient epimerization/saponification sequence of 4 which sets both stereocenters ...