title: Simple, versatile and highly diastereoselective synthesis of 1,3,4-trisubstituted-2-oxopiperazine-containing peptidomimetic precursors.
abstract: The selective O-deprotection of (1'S)-4-(tert-butoxycarbonyl)-1-[1'-phenylmethyloxymethyl-2'-[(tert-butyldimethylsilyl)oxy]ethyl]-2-oxopiperazine furnished an enantiomerically pure alcohol whose regio- and diastereoselective C3-alkylation yielded either (3R)- or (3S)-1,3,4-trisubstituted-2-oxopiperazines in high diastereomeric purity. These derivatives were efficiently transformed into (1'R)- or (1'S)-peptide templates utilizable to prepare peptidomimetics. This method provides easy access to each 1,3,4-trisubstituted-2-oxopiperazine diastereomer and facilitates, through the large choice of substituents at the 3-position together with the chemistry that can be performed on the N1 substituent, the preparation of a large number of diastereomerically pure constrained peptidomimetics from a single precursor.
authors.affiliation: Laboratoire de Chimie Thérapeutique, EA 2629, 1 Rue des Louvels, 80000, Amiens, France.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Franceschini
authors.forename: Pascal
authors.initials: P
authors.lastname: Sonnet
authors.forename: Dominique
authors.initials: D
authors.lastname: Guillaume
mesh_terms: D007769:Lactams / Q000138:chemical synthesis / Q000737:chemistry; D018716:Molecular Mimicry; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007769:Lactams; D010455:Peptides; D010879:Piperazines