First enantiospecific synthesis of marine sesquiterpene quinol akaol A |
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Authors: | Alvarez-Manzaneda Enrique Chahboun Rachid Alvarez Esteban Fernández Antonio Alvarez-Manzaneda Ramón Haidour Ali Ramos Jose Miguel Akhaouzan Ali |
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Affiliation: | Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, Spain. eamr@ugr.es |
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Abstract: | 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. |
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