1,3-Dipolar cycloaddition of a cyclic nitrone derived from 2-deoxy-D-ribose to α,β-unsaturated lactones: An entry to carbapenem antibiotics
| Autor: | Michał Pieczykolan, Bartłomiej Furman, Marek Chmielewski, Olga Staszewska-Krajewska |
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| Rok vydání: | 2016 |
| Předmět: |
Stereochemistry
Salt (chemistry) beta-Lactams 010402 general chemistry Ring (chemistry) 01 natural sciences Biochemistry Analytical Chemistry Nitrone Lactones Carbapenem Antibiotics Molecule Bond cleavage chemistry.chemical_classification Cycloaddition Reaction Molecular Structure Deoxyribose 010405 organic chemistry Chemistry Organic Chemistry Stereoisomerism General Medicine 0104 chemical sciences Carbapenems 1 3-Dipolar cycloaddition Nitrogen Oxides Lactone |
| Zdroj: | Carbohydrate Research. 433:89-96 |
| ISSN: | 0008-6215 |
| DOI: | 10.1016/j.carres.2016.07.002 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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