title: 1,3-Dipolar cycloaddition of a cyclic nitrone derived from 2-deoxy-D-ribose to α,β-unsaturated lactones: An entry to carbapenem antibiotics.
abstract: 1,3-Dipolar cycloadditions of 2-deoxy-D-ribose-derived L-threo five-membered cyclic nitrone to α,β-unsaturated γ- and δ-lactones were investigated. Cycloadducts obtained from δ-lactones, after NO bond cleavage, opening of the lactone ring, and protection of hydroxyl groups were subjected to β-lactam ring formation by using Mukaiyama's salt. Cycloadducts from γ-lactones subjected to the same reaction sequence undergo β-elimination of a water molecule to provide pyrrolidine-substituted unsaturated γ-lactones.
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
authors.forename: Michał
authors.initials: M
authors.lastname: Pieczykolan
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
authors.forename: Olga
authors.initials: O
authors.lastname: Staszewska-Krajewska
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
authors.forename: Bartłomiej
authors.initials: B
authors.lastname: Furman
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland. Electronic address: marek.chmielewski@icho.edu.pl.
authors.forename: Marek
authors.initials: M
authors.lastname: Chmielewski
mesh_terms: D015780:Carbapenems / Q000138:chemical synthesis / Q000737:chemistry; D061565:Cycloaddition Reaction; D003855:Deoxyribose / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D015780:Carbapenems; D007783:Lactones; D009589:Nitrogen Oxides; D047090:beta-Lactams; C015388:nitrones; D003855:Deoxyribose
keywords: 1,3-Dipolar cycloaddition; Nitrones; β-Lactams; γ- and δ-unsaturated lactones