Browsing by Subject "Organic synthesis"
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- PublicationOpen AccessDiastereoselective Intramolecular Heck Reaction Assisted by an Acetate Group: Synthesis of the Decahydrobenzofluorene Derivative Dasyscyphin E(American Chemical Society, 2017-08-15) Jimenez, Fermin; Fernandez, Antonio; Boulifa, Ettahir; Mansour, Ahmed Ibn; Alvarez-Manzaneda, Ramon; Chahboun, Rachid; Alvarez-Manzaneda, Enrique; Química OrgánicaThe 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.
PublicationOpen AccessFAIR data for compunds included in the article "Maximizing the [c2]daisy chain to lasso ratio through competitive self-templating clipping reactions"(Universidad de Murcia, 2021-11-30) Saura-Sanmartin, Adrian; Pastor Vivero, Aurelia; Martinez-Cuezva, Alberto; Berná Cánovas, José; Química Orgánica