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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
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02375819
Contributor : François Estour <>
Submitted on : Friday, November 22, 2019 - 11:09:50 AM
Last modification on : Thursday, August 27, 2020 - 1:43:08 AM

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Bernardin Akagah, François Estour, Philippe Vérité, Pedro Lameiras, Mohammed Nour, et al.. Regio- and diastereocontrolled preparative oxidation of methyloctalones by a biomimetic porphyrin catalyst. Chirality, Wiley, 2004, 16 (6), pp.398-403. ⟨10.1002/chir.20043⟩. ⟨hal-02375819⟩

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