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Novel Baeyer–Villiger-type oxidation of 4,5-epoxymorphinan derivatives

[Display omitted] •A novel molecular oxygen-mediated Baeyer–Villiger-type oxidation has been discovered.•The reaction proceeds specifically to the morphinan skeleton.•The products would be useful for designing highly selective and potent KOR agonists. A novel molecular oxygen-mediated Baeyer–Villige...

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Bibliographic Details
Published in:Tetrahedron letters 2021-01, Vol.63, p.152714, Article 152714
Main Authors: Hino, Tsubasa, Kutsumura, Noriki, Saitoh, Tsuyoshi, Yamamoto, Naoshi, Nagumo, Yasuyuki, Mogi, Yuzo, Watanabe, Yoshikazu, Nagase, Hiroshi
Format: Article
Language:English
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Summary:[Display omitted] •A novel molecular oxygen-mediated Baeyer–Villiger-type oxidation has been discovered.•The reaction proceeds specifically to the morphinan skeleton.•The products would be useful for designing highly selective and potent KOR agonists. A novel molecular oxygen-mediated Baeyer–Villiger-type oxidation specific to the morphinan skeleton has been discovered. The reaction of a ketone bearing a bicyclo[2.2.2]octenone skeleton with KOH (pellet) in refluxing tBuOH under an oxygen atmosphere (balloon) afforded unexpected cyclopropanecarboxylic acid and ketolactone derivatives. The reactive sites (carboxylic acid and ester) in those products are oriented over the C-ring in the morphinan skeleton, and thus such morphinan compounds would be useful intermediates to design ideal κ opioid receptor agonists.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.152714