title: Total Synthesis of (-)-Bacchopetiolone via an Asymmetric Hydroxylative Phenol Dearomatization/[4+2]-Dimerization Cascade Promoted by a Novel Salen-Type Chiral Iodane.
abstract: The first total and biomimetic synthesis of the natural bis(sesquiterpene) (-)-bacchopetiolone (revised structure) was completed through a highly diastereoselective hydroxylative phenol dearomatization/[4+2]-dimerization cascade conversion of (+)-curcuphenol using a novel C2-symmetrical chiral Salen-type bis(λ(5)-iodane).
authors.affiliation: Univ. Bordeaux , ISM (CNRS-UMR 5255), 351 cours de la Libération, Talence F-33405 Cedex, France.
authors.forename: Romain
authors.initials: R
authors.lastname: Coffinier
authors.affiliation: Univ. Bordeaux , ISM (CNRS-UMR 5255), 351 cours de la Libération, Talence F-33405 Cedex, France.
authors.forename: Mourad
authors.initials: M
authors.lastname: El Assal
authors.affiliation: Univ. Bordeaux , ISM (CNRS-UMR 5255), 351 cours de la Libération, Talence F-33405 Cedex, France.
authors.forename: Philippe A
authors.initials: PA
authors.lastname: Peixoto
authors.affiliation: Univ. Bordeaux , ISM (CNRS-UMR 5255), 351 cours de la Libération, Talence F-33405 Cedex, France.
authors.forename: Cyril
authors.initials: C
authors.lastname: Bosset
authors.affiliation: Univ. Pau et Pays de l'Adour , IPREM (CNRS-UMR 5254), Hélioparc, 2 avenue Pierre Angot, Pau F-64053 Cedex 09, France.
authors.forename: Karinne
authors.initials: K
authors.lastname: Miqueu
authors.affiliation: Univ. Pau et Pays de l'Adour , IPREM (CNRS-UMR 5254), Hélioparc, 2 avenue Pierre Angot, Pau F-64053 Cedex 09, France.
authors.forename: Jean-Marc
authors.initials: JM
authors.lastname: Sotiropoulos
authors.affiliation: Univ. Bordeaux , ISM (CNRS-UMR 5255), 351 cours de la Libération, Talence F-33405 Cedex, France.
authors.forename: Laurent
authors.initials: L
authors.lastname: Pouységu
authors.affiliation: Univ. Bordeaux , ISM (CNRS-UMR 5255), 351 cours de la Libération, Talence F-33405 Cedex, France.
authors.forename: Stéphane
authors.initials: S
authors.lastname: Quideau
mesh_terms: D000098:Acetophenones / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000098:Acetophenones; D010636:Phenols; D012717:Sesquiterpenes; C522746:bacchopetiolone; C054389:curcuphenol