title: Revised structure, total synthesis, and absolute configuration of kopeolin and kopeolone.
abstract: An enantioselective total synthesis of two sesquiterpenoids, kopeolin and kopeolone, has been achieved. Using the diastereoselective addition of an organocerate as a key step, we controlled the absolute stereochemistry of a crucial stereocenter present in these natural products. This approach allowed us to confirm a structural revision that we previously proposed (Chem.-Eur. J. 2013, 19, 10632-10642) and to fully characterize these natural products while elucidating their absolute stereochemistry.
authors.affiliation: Aix Marseille Université , CNRS, ICR UMR 7273, 13397, Marseille, France.
authors.forename: Stéphanie
authors.initials: S
authors.lastname: Miquet
authors.forename: Paul
authors.initials: P
authors.lastname: Brémond
authors.forename: Benjamin
authors.initials: B
authors.lastname: Ayela
authors.forename: Sylvain R A
authors.initials: SR
authors.lastname: Marque
authors.forename: Gérard
authors.initials: G
authors.lastname: Audran
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D012717:Sesquiterpenes; C587416:kopeolin; C587415:kopeolone