Straighforward Synthesis of a Novel Chiron and its Application to the Synthesis of (+)-1,4-Dideoxymannojirimycin and Further Polyoxygenated 2-Pyperidones
| Autor: | Fernando Sartillo-Piscil, Rosa L. Meza-León, Herbert Höpfl, Silvano Cruz-Gregorio, Leticia Quintero, Elsie Ramirez |
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| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Aqueous solution 010405 organic chemistry Chemistry Stereochemistry Total synthesis General Chemistry 010402 general chemistry Furanose 01 natural sciences 0104 chemical sciences chemistry.chemical_compound Enantiopure drug Organic chemistry Moiety Stereoselectivity Bond cleavage Derivative (chemistry) |
| Zdroj: | ChemistrySelect. 2:546-549 |
| ISSN: | 2365-6549 |
| Popis: | The total synthesis of (+)-1,4-dideoxymannojimycin and the enantiopure synthesis of three polyoxygenated piperidin-2-ones from a novel chiron is reported. Starting from 3-deoxy-3-amine-D-glucose, by means of the stereoselective aqueous SHOWO protocol (Sequential-Hydrolysis-Oxidation-Wittig Olefination), the unsaturated-7,3-lactam-D-xylofuranose derivative was prepared, which depending on the oxidative C−C bond cleavage reaction conditions for the furanose moiety, is transformed into either (+)-1,4-dideoxymannojirimycin or polyoxygenated piperidin-2-ones. |
| Databáze: | OpenAIRE |
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