title: A general approach to (5S,6R)-6-alkyl-5-benzyloxy-2-piperidinones: application to the asymmetric syntheses of neurokinin substance P receptor antagonist (-)-L-733,061 and (-)-deoxocassine.
abstract: A general approach to (5S,6R)-6-alkyl-5-benzyloxy-2-piperidinones based on the regio- and diastereoselective reductive alkylation of (S)-3-benzyloxyglutarimide 7 is described. This method opens an entrance to chiral nonracemic substituted 3-piperidinols. The versatility of the method is illustrated by the asymmetric syntheses of neurokinin substance P receptor antagonist L-733,061 (ent-1), (-)-deoxocassine (4), and an inhibitor of HIV proteases (5a).
authors.affiliation: Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005, P. R. China.
authors.forename: Liang-Xian
authors.initials: LX
authors.lastname: Liu
authors.forename: Yuan-Ping
authors.initials: YP
authors.lastname: Ruan
authors.forename: Zheng-Qing
authors.initials: ZQ
authors.lastname: Guo
authors.forename: Pei-Qiang
authors.initials: PQ
authors.lastname: Huang
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D017320:HIV Protease Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D015394:Molecular Structure; D064729:Neurokinin-1 Receptor Antagonists; D010880:Piperidines / Q000138:chemical synthesis* / Q000494:pharmacology; D013237:Stereoisomerism; D013373:Substance P / Q000037:antagonists & inhibitors*
chemical_list: D017320:HIV Protease Inhibitors; D064729:Neurokinin-1 Receptor Antagonists; D010880:Piperidines; C492728:deoxocassine; C103788:3-((3,5-bis(trifluoromethyl)phenyl)methyloxy)-2-phenylpiperidine; D013373:Substance P