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https://doi.org/10.1021/acs.joc.7b01551
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Título: | Diastereoselective Intramolecular Heck Reaction Assisted by an Acetate Group: Synthesis of the Decahydrobenzofluorene Derivative Dasyscyphin E |
Fecha de publicación: | 15-ago-2017 |
Editorial: | American Chemical Society |
ISSN: | 0022-3263 |
Palabras clave: | Sesquiterpenes Organic synthesis Organic compounds Cyclization, Stereoselectivity |
Resumen: | The first synthesis of antifungal sesquiterpene quinol dasyscyphin E was achieved starting from trans-communic acid. The process described involves the first diastereoselective synthesis of this type of compound by cyclization of an aryl bicyclosesquiterpene. The acid was efficiently transformed into a sesquiterpene synthon, which was converted into the corresponding bromoaryl sesquiterpene. The key step of synthetic sequence was the cyclization of the latter under Heck reaction conditions, which yielded the tetracyclic skeleton of the target compound with complete diastereoselectivity. The participation of an acetate group is decisive, both for the course of the Heck reaction and for the stereoselectivity of the process. |
Autor/es principal/es: | Jimenez, Fermin Fernandez, Antonio Boulifa, Ettahir Mansour, Ahmed Ibn Alvarez-Manzaneda, Ramon Chahboun, Rachid Alvarez-Manzaneda, Enrique |
URI: | http://hdl.handle.net/10201/113652 |
DOI: | https://doi.org/10.1021/acs.joc.7b01551 |
Tipo de documento: | info:eu-repo/semantics/article |
Número páginas / Extensión: | 11 |
Derechos: | info:eu-repo/semantics/openAccess Attribution-NonCommercial-NoDerivatives 4.0 Internacional |
Aparece en las colecciones: | Artículos: Química Orgánica |
Ficheros en este ítem:
Fichero | Descripción | Tamaño | Formato | |
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2 JOC 2017.pdf | 1,54 MB | Adobe PDF | Visualizar/Abrir |
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