First enantiospecific synthesis of marine sesquiterpene quinol akaol A
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Alvarez-Manzaneda, Enrique; Chahboun, Rachid; Alvarez, Esteban; Fernández, Antonio; Alvarez-Manzaneda Roldán, Ramón Jesús; [et al.]Fecha
2011-10-27Resumen
The first enantiospecific synthesis of akaol A, a marine sesquiterpene quinol, has been achieved. Key steps of the synthetic sequence are the oxidative degradation of (-)-sclareol to a dinorlabdane ketoester, mediated by the ozone–lead(IV) acetate system, the diastereoselective α-methylation of a ketoaldehyde, followed by an intramolecular aldol condensation and the further Diels–Alder cycloaddition of a dienol ether.