title: First enantiospecific synthesis of marine sesquiterpene quinol akaol A.
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.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, Spain. eamr@ugr.es
authors.forename: Enrique
authors.initials: E
authors.lastname: Alvarez-Manzaneda
authors.forename: Rachid
authors.initials: R
authors.lastname: Chahboun
authors.forename: Esteban
authors.initials: E
authors.lastname: Alvarez
authors.forename: Antonio
authors.initials: A
authors.lastname: Fernández
authors.forename: Ramón
authors.initials: R
authors.lastname: Alvarez-Manzaneda
authors.forename: Ali
authors.initials: A
authors.lastname: Haidour
authors.forename: Jose Miguel
authors.initials: JM
authors.lastname: Ramos
authors.forename: Ali
authors.initials: A
authors.lastname: Akhaouzan
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D010084:Oxidation-Reduction; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D011809:Quinones; D012717:Sesquiterpenes