Blue light photoredox decarboxylation and tin-free Barton-McCombie reactions in the stereoselective synthesis of (+)-muscarine
| Autor: | Fernando Sartillo-Piscil, Leticia Quintero, Silvano Cruz-Gregorio, Dulce M. Tepox-Luna, Victoria Rodríguez-Tzompanzi |
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| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Anomer Muscarine 010405 organic chemistry Decarboxylation Organic Chemistry Glycoside 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Drug Discovery Stereoselectivity Deoxygenation Derivative (chemistry) Methyl group |
| Zdroj: | Tetrahedron Letters. 60:423-426 |
| ISSN: | 0040-4039 |
| Popis: | Starting from a 1,2-O-isopropylidene-α- d -xylofuranose derivative, a non-toxic free-radical approach for the synthesis of (+)-muscarine is reported. To this end, a stereoselective allylation reaction at the anomeric position of a respective xylofuranose derivative was employed as a new synthetic strategy for the installation of the methyl group at the C-5 position of (+)-muscarine. Accordingly, the allyl group was transformed into the methyl group in three sequential steps highlighting a blue-light photoredox decarboxylation reaction. Additionally, a tin-free Barton-McCombie deoxygenation reaction of the respective C-methyl glycoside allowed the completion of this free-radical approach to (+)-muscarine. |
| Databáze: | OpenAIRE |
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