Diastereoselective additions of allylmetal reagents to free and protected syn-α,β-dihydroxyketones enable efficient synthetic routes to methyl trioxacarcinoside A
| Autor: | Jakub Svenda, Andrew G. Myers, Daniel J. Smaltz |
|---|---|
| Rok vydání: | 2012 |
| Předmět: |
chemistry.chemical_classification
Ketone Molecular Structure Chemistry Organic Chemistry Substituent Substrate (chemistry) Stereoisomerism Glycosidic bond Ketones Biochemistry Coupling reaction Article Silyl ether chemistry.chemical_compound Reagent Organic chemistry Indicators and Reagents Glycosides Physical and Theoretical Chemistry Chelating Agents |
| Zdroj: | Organic letters. 14(7) |
| ISSN: | 1523-7052 |
| Popis: | Two routes to the 2,6-dideoxysugar methyl trioxacarcinoside A are described. Each was enabled by an apparent α-chelation-controlled addition of an allylmetal reagent to a ketone substrate containing a free α-hydroxyl group and a β-hydroxyl substituent, either free or protected as the corresponding di-tert-butylmethyl silyl ether. Both routes provide practical access to gram quantities of trioxacarcinose A in a form suitable for glycosidic coupling reactions. |
| Databáze: | OpenAIRE |
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