Synthesis and functionalization of bicyclic N,O-acetal scaffolds from furfural
| Autor: | Ferdi van der Pijl, Floris P. J. T. Rutjes, Floris L. van Delft |
|---|---|
| Rok vydání: | 2015 |
| Předmět: |
Aza Compounds
Molecular Structure Bicyclic molecule Organic Chemistry Clinical Biochemistry Acetal Pharmaceutical Science Stereoisomerism Synthetic Organic Chemistry Furfural Biochemistry Catalysis Bridged Bicyclo Compounds chemistry.chemical_compound Acetals chemistry Nucleophile Drug Discovery Functional group Molecular Medicine Surface modification Organic chemistry Furaldehyde Azo Compounds Molecular Biology |
| Zdroj: | Bioorganic & Medicinal Chemistry, 23, 2721-2729 Bioorganic & Medicinal Chemistry, 23, 11, pp. 2721-2729 |
| ISSN: | 0968-0896 |
| DOI: | 10.1016/j.bmc.2014.12.045 |
| Popis: | We have synthesized biologically relevant 6-aza-8-oxa[3.2.1]bicyclooctane scaffolds in a five-step procedure starting from furfural. Besides showing that these scaffolds are amenable to decoration via standard functional group interconversions, we also describe investigations for further functionalization via Lewis acid-mediated N,O-acetal opening, followed by nucleophilic trapping of the resulting intermediate cation. By using different nucleophiles, we have successfully prepared a modest library of 2,6-trans-disubstituted pyrans in good yields and in a highly diastereoselective manner. |
| Databáze: | OpenAIRE |
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