Regio- and diastereocontrolled preparative oxidation of methyloctalones by a biomimetic porphyrin catalyst.
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.
Akagah
Bernardin
B
Département de Chimie Organique Pharmaceutique, Faculté de Médecine et de Pharmacie de Rouen, Rouen, France.
Estour
François
F
Vérité
Philippe
P
Lameiras
Pédro
P
Nour
Mohammed
M
Cavé
Christian
C
Ménager
Sabine
S
Lafont
Olivier
O
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
D005561:Formates; D008665:Metalloporphyrins; D009281:Naphthalenes; D011166:Porphyrins; D013256:Steroids; C488403:methyloctalone; C030544:formic acid; D010100:Oxygen