Conjugate Addition to Phenylglycinol-Derived Unsaturated ä-Lactams. Enantioselective Synthesos of Uleine Alkaloids
The stereochemical outcome of the conjugate addition of a variety of stabilized nucleophiles (2indoleaceticenolatesandsulfur-stabilizedanions)tothephenylglycinol-derivedunsaturatedlactams trans-2, cis-2, and its 8-ethyl-substituted analogue 10 is studied. The factors governing the exo or endo facial...
| Autores: | , , , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2004 |
| País: | España |
| Institución: | Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya) |
| Repositorio: | Recercat. Dipósit de la Recerca de Catalunya |
| OAI Identifier: | oai:recercat.cat:2445/159897 |
| Acceso en línea: | https://hdl.handle.net/2445/159897 |
| Access Level: | acceso abierto |
| Palabra clave: | Alcaloides Lactames Síntesi orgànica Alkaloids Lactams Organic synthesis |
| Sumario: | The stereochemical outcome of the conjugate addition of a variety of stabilized nucleophiles (2indoleaceticenolatesandsulfur-stabilizedanions)tothephenylglycinol-derivedunsaturatedlactams trans-2, cis-2, and its 8-ethyl-substituted analogue 10 is studied. The factors governing the exo or endo facial stereoselectivity are discussed. This methodology provides short synthetic routes to either cis- ortrans-3,4-disubstituted enantiopure piperidines as well as efficient routes for the enantioselective construction of the tetracyclic ring system of uleine alkaloids, both in the normal and 20-epi series. The formal total synthesis of several alkaloids of this group is reported. |
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