A new cross-coupling-based synthesis of carpanone.
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.
Liron
Frédéric
F
Institut Parisien de Chimie Moléculaire UMR CNRS 7201, FR2769 Institut de Chimie Moléculaire, UPMC Univ Paris 06, Place Jussieu, 75005, Boite 183, Paris, France.
Fontana
Francesco
F
Zirimwabagabo
Jean-Olivier
JO
Prestat
Guillaume
G
Rajabi
Jamshid
J
La Rosa
Concetta
C
Poli
Giovanni
G
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
D006576:Heterocyclic Compounds, 4 or More Rings; C532598:carpanone; D010165:Palladium