Issue 92, 2018

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

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

Supplementary files

Article information

Article type
Communication
Submitted
24 set 2018
Accepted
10 out 2018
First published
05 nov 2018

Chem. Commun., 2018,54, 13018-13021

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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