title: Development of a stereoselective Ugi reaction starting from an oxanorbornene β-amino acid derivative.
abstract: We have synthesised a novel oxanorbornene β-aminoacid derivative and employed it in a stereoselective Ugi reaction. Hypothesis regarding the mechanism taking place during the reaction have been made and validated through the determination of the relative and absolute configuration of the Ugi adducts. Use of the correct choice of solvents can increase stereoselection. The resulting bicyclic peptidomimetics can be used as a novel class of pluripotent substrates to be elaborated according to the synthetic strategies previously elaborated in our laboratories.
authors.affiliation: Università degli Studi di Genova, Dipartimento di Chimica e Chimica Industriale, Genova, Italy.
authors.forename: Luca
authors.initials: L
authors.lastname: Banfi
authors.forename: Andrea
authors.initials: A
authors.lastname: Basso
authors.forename: Cinzia
authors.initials: C
authors.lastname: Chiappe
authors.forename: Fabio
authors.initials: F
authors.lastname: De Moliner
authors.forename: Renata
authors.initials: R
authors.lastname: Riva
authors.forename: Lorenzo
authors.initials: L
authors.lastname: Sonaglia
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D015394:Molecular Structure; D012263:Ribonucleosides / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D012263:Ribonucleosides; C032886:oxanosine