Facile synthesis of azocino[4,3-b]indoles by ring-closing metathesis
The azocino[4,3-b]indole system, tricyclic substructure of the indole alkaloids apparicine and ervaticine, is efficiently assembled by ring-closing metathesis of 2-allyl-3-(allylaminomethyl)indoles. The metathesis sites are introduced into the indole nucleus by reductive amination of a 3-formyl deri...
| Autores: | , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2007 |
| País: | España |
| Institución: | Universidad de Barcelona |
| Repositorio: | Dipòsit Digital de la UB |
| OAI Identifier: | oai:diposit.ub.edu:2445/160425 |
| Acceso en línea: | https://hdl.handle.net/2445/160425 |
| Access Level: | acceso abierto |
| Palabra clave: | Alcaloides Metàtesi (Química) Síntesi orgànica Alkaloids Metathesis (Chemistry) Organic synthesis |
| Sumario: | The azocino[4,3-b]indole system, tricyclic substructure of the indole alkaloids apparicine and ervaticine, is efficiently assembled by ring-closing metathesis of 2-allyl-3-(allylaminomethyl)indoles. The metathesis sites are introduced into the indole nucleus by reductive amination of a 3-formyl derivative with allylamine, followed by a-lithiation with subsequent electrophilic trapping with acrolein. |
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