title: Synthesis of d- and l-2,3-trans-3,4-cis-4,5-trans-3,4-dihydroxy-5-hydroxymethylproline and tripeptides containing them.
abstract: Enantiomerically pure (-)-(1R,4R,5R,6S)- and (+)-(1S,4S,5S,6R)-7-(tert-butoxycarbonyl)-5,6-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]hept-2-one ((-)-3 and (+)-3) have been obtained from the Diels-Alder adduct of N-(tert-butoxycarbonyl)pyrrole and 2-bromo-1-(p-toluenesulfonyl)acetylene, including the Alexakis optical resolution of ketone (+/-)-3 via formation of cyclic aminals with (1R,2R)-diphenylethylenediamine. Compounds (-)-3 and (+)-3 were converted into d- and l-2,3-trans-3,4-cis-4,5-trans-N-(tert-butoxycarbonyl)-5-hydroxymethyl-3,4-isopropylidenedioxyprolines (-)-4 and (+)-4, respectively. Applying the Boc and Fmoc strategies of peptide synthesis, these compounds were used to construct two tripeptides containing the d- or l-2,3-trans-3,4-cis-4,5-trans-3,4-dihydroxy-5-hydroxymethylproline.
authors.affiliation: Laboratoire de Glycochimie et de Synthèse Asymétrique, Swiss Federal Institute of Technology (EPFL), BCH, CH-1015 Lausanne-Dorigny, Switzerland. ajmoreno@us.es
authors.forename: Antonio J
authors.initials: AJ
authors.lastname: Moreno-Vargas
authors.forename: Inmaculada
authors.initials: I
authors.lastname: Robina
authors.forename: Elena
authors.initials: E
authors.lastname: Petricci
authors.forename: Pierre
authors.initials: P
authors.lastname: Vogel
mesh_terms: D008968:Molecular Conformation; D009842:Oligopeptides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009842:Oligopeptides