Stereocontrolled preparation of a nonpeptidal (-)-spirobicyclic NK-1 receptor antagonist
The synthesis of a spirobicyclic NK-1 receptor (Substance-P) antagonist 1 antipode is described. Retrosynthetic analysis reveals an allylic halide A bearing the cyclopropoxy-substituted aryl group and a 2-phenyl-3-piperidone B. The stereochemistry in the spirobicyclic system bearing three chiral centers is initially set via a highly diastereoselective zinc-mediated coupling of the allylic bromide 23 to the optically active ketopiperidine 3. The remaining benzylic asymmetric center is set by a diastereoselective hydroboration followed by cyclization to the spirobicyclic system.
Maligres, Peter E.,Waters, Marjorie M.,Lee, Jaemoon,Reamer, Robert A.,Askin, David,Ashwood, Michael S.,Cameron, Mark
p. 1093 - 1101
(2007/10/03)
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