Stereoselective synthesis of cis-1,3-dimethyltetrahydroisoquinolines: formal synthesis of naphthylisoquinoline alkaloids
Starting from tricyclic lactam 2, which is easily accessible by cyclocondensation of -oxoester 1 with (R)-phenylglycinol, a three-step synthetic route to enantiopure 1-substituted tetrahydroisoquinolines, including 1-alkyl-, 1-aryl-, and 1-benzyl- tetrahydroisoquinoline alkaloids as well as the tri...
| Autores: | , , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2012 |
| 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:2445/164259 |
| Acceso en línea: | https://hdl.handle.net/2445/164259 |
| Access Level: | acceso abierto |
| Palabra clave: | Síntesi asimètrica Alcaloides Lactames Asymmetric synthesis Alkaloids Lactams |
| Sumario: | Starting from tricyclic lactam 2, which is easily accessible by cyclocondensation of -oxoester 1 with (R)-phenylglycinol, a three-step synthetic route to enantiopure 1-substituted tetrahydroisoquinolines, including 1-alkyl-, 1-aryl-, and 1-benzyl- tetrahydroisoquinoline alkaloids as well as the tricyclic alkaloid (-)-crispine A, has been developed. The key step is a stereoselective -amidoalkylation reaction using the appropriate Grignard reagent. |
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