title: Regio- and diastereocontrolled preparative oxidation of methyloctalones by a biomimetic porphyrin catalyst.
abstract: Both enantiomers of methyloctalone were oxidized by a biomimetic manganese/porphyrin/imidazole catalytic system in order to obtain sufficient amounts of various model metabolites. The double bond proved to be less sensitive than the ring methylenes. Hydroxylation occurred mainly in the allylic position (position 8) and also at positions 7 and 6. In position 8, two diastereomers were obtained while in positions 7 and 6 the reaction was diastereospecific. In the case of position 8 only the oxidation yielded a keto compound. The efficiency of this method for the preparation of functionalized chiral synthons was better than it was for biological pathways.
authors.affiliation: Département de Chimie Organique Pharmaceutique, Faculté de Médecine et de Pharmacie de Rouen, Rouen, France.
authors.forename: Bernardin
authors.initials: B
authors.lastname: Akagah
authors.forename: François
authors.initials: F
authors.lastname: Estour
authors.forename: Philippe
authors.initials: P
authors.lastname: Vérité
authors.forename: Pédro
authors.initials: P
authors.lastname: Lameiras
authors.forename: Mohammed
authors.initials: M
authors.lastname: Nour
authors.forename: Christian
authors.initials: C
authors.lastname: Cavé
authors.forename: Sabine
authors.initials: S
authors.lastname: Ménager
authors.forename: Olivier
authors.initials: O
authors.lastname: Lafont
mesh_terms: D032701:Biomimetics; D002384:Catalysis; D005561:Formates / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008665:Metalloporphyrins; D008956:Models, Chemical; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry* / Q000378:metabolism; D011166:Porphyrins / Q000737:chemistry*; D013237:Stereoisomerism; D013256:Steroids / Q000737:chemistry*; D013696:Temperature
chemical_list: D005561:Formates; D008665:Metalloporphyrins; D009281:Naphthalenes; D011166:Porphyrins; D013256:Steroids; C488403:methyloctalone; C030544:formic acid; D010100:Oxygen