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Issue 92, 2018
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A desymmetrization-based approach to morphinans: application in the total synthesis of oxycodone

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Abstract

Here we report a total synthesis of the pharmacologically significant morphinan alkaloid, oxycodone. The centerpiece of the developed strategy features the first application of the Rovis desymmetrization of peroxyquinol in target-oriented total synthesis to access an optically active phenanthrene framework shared by the morphinans. A Stork–Ueno radical cyclization under photoredox conditions installed the all-carbon quaternary stereocenter, and a late-stage reductive detosylation with concomitant piperidine formation secured the core structure of the target molecule.

Graphical abstract: A desymmetrization-based approach to morphinans: application in the total synthesis of oxycodone

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Publication details

The article was received on 24 Sep 2018, accepted on 10 Oct 2018 and first published on 05 Nov 2018


Article type: Communication
DOI: 10.1039/C8CC07667G
Citation: Chem. Commun., 2018,54, 13018-13021
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    A desymmetrization-based approach to morphinans: application in the total synthesis of oxycodone

    K. H. (. Park and D. Y.-K. Chen, Chem. Commun., 2018, 54, 13018
    DOI: 10.1039/C8CC07667G

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