title: A new cross-coupling-based synthesis of carpanone.
abstract: Carpanone has been stereoselectively synthesized in 55% yield and six steps from sesamol. The key step of the synthetic sequence is the direct introduction of the propenyl side chain via a Suzuki-Miyaura cross-coupling reaction. The subsequent Pd(II)-catalyzed oxidative coupling yields carpanone as a single diastereoisomer independently of the geometric configuration of the starting precursor. A new mechanism is proposed for this transformation.
authors.affiliation: Institut Parisien de Chimie Moléculaire UMR CNRS 7201, FR2769 Institut de Chimie Moléculaire, UPMC Univ Paris 06, Place Jussieu, 75005, Boite 183, Paris, France.
authors.forename: Frédéric
authors.initials: F
authors.lastname: Liron
authors.forename: Francesco
authors.initials: F
authors.lastname: Fontana
authors.forename: Jean-Olivier
authors.initials: JO
authors.lastname: Zirimwabagabo
authors.forename: Guillaume
authors.initials: G
authors.lastname: Prestat
authors.forename: Jamshid
authors.initials: J
authors.lastname: Rajabi
authors.forename: Concetta
authors.initials: C
authors.lastname: La Rosa
authors.forename: Giovanni
authors.initials: G
authors.lastname: Poli
mesh_terms: D002384:Catalysis; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; C532598:carpanone; D010165:Palladium