An Enantioselective Organocatalytic Approach to Both Enantiomers of Lasubine II
| Autor: | Marian M. J. H. P. Willems, Floris L. van Delft, Ferdi van der Pijl, Jorge M. M. Verkade, Floris P. J. T. Rutjes, Peter J. L. M. Quaedflieg |
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| Rok vydání: | 2009 |
| Předmět: |
Magnetic Resonance Spectroscopy
Quinolizidine Molecular Structure Proline Bicyclic molecule Chemistry Stereochemistry Organic Chemistry Enantioselective synthesis Stereoisomerism Synthetic Organic Chemistry Metathesis Chemical synthesis Catalysis chemistry.chemical_compound Alkaloids Cyclization Stereoselectivity Enantiomer Mannich reaction Quinolizines |
| Zdroj: | Journal of Organic Chemistry, 74, 3207-3210 Journal of Organic Chemistry, 74, 8, pp. 3207-3210 |
| ISSN: | 0022-3263 |
| DOI: | 10.1021/jo900141f |
| Popis: | A concise stereoselective route providing access to both enantiomers of the bioactive quinolizidine alkaloid lasubine II has been developed. The enantioselectivity was introduced by taking advantage of a proline-catalyzed asymmetric Mannich reaction. Next, the bicyclic system was constructed via a diastereoselective Mannich cyclization and subsequent ring-closing metathesis as the key steps. |
| Databáze: | OpenAIRE |
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