A practical synthesis of a γ-secretase inhibitor

…, CJ McWilliams, GW Stewart, RD Wilson…

Index: Scott, Jeremy P.; Lieberman, David R.; Beureux, Olivier M.; Brands, Karel M. J.; Davies, Antony J.; Gibson, Andrew W.; Hammond, Deborah C.; McWilliams, Chris J.; Stewart, Gavin W.; Wilson, Robert D.; Dolling, Ulf-H. Journal of Organic Chemistry, 2007 , vol. 72, # 11 p. 4149 - 4155

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Citation Number: 14

Abstract

A practical and scaleable synthesis of the γ-secretase inhibitor 1 is reported. The inhibitor consists of a central trisubstituted cyclohexane core with appended propionic acid, 2, 5- difluorophenyl, and 4-chlorophenylsulfonyl moieties. Two alternative synthetic strategies, proceeding by way of a common disubstituted cyclohexanone derivative 5, were studied. In the preferred route, conjugate reduction of acrylonitrile derivative 4 with L-Selectride ...