Enantioselective de novo synthesis of 14-hydroxy-6-oxomorphinans

Jonathan C. Moore; Louis Modell; Jacqueline R. Glenn; Kieran D. Jones; Stephen P. Argent; J. Robert Lane; Meritxell Canals; Hon Wai Lam

doi:10.1039/D4CC01788A

Enantioselective de novo synthesis of 14-hydroxy-6-oxomorphinans†

Jonathan C. Moore,

^ab Louis Modell,^c Jacqueline R. Glenn,^de Kieran D. Jones,

^ab Stephen P. Argent,

^b J. Robert Lane,^de Meritxell Canals^de and Hon Wai Lam

*^ab

Author affiliations

* Corresponding authors

^a The GlaxoSmithKline Carbon Neutral Laboratories for Sustainable Chemistry, University of Nottingham, Jubilee Campus, Triumph Road, Nottingham, UK
E-mail: hon.lam@nottingham.ac.uk

^b School of Chemistry, University of Nottingham, University Park, Nottingham, UK

^c School of Pharmacy, University of Nottingham Biodiscovery Institute, University of Nottingham, Nottingham, UK

^d Division of Physiology, Pharmacology and Neuroscience, School of Life Sciences, Queen's Medical Centre, University of Nottingham, Nottingham, UK

^e Centre of Membrane Protein and Receptors, Universities of Birmingham and Nottingham, The Midlands, UK

Abstract

The enantioselective de novo synthesis of pharmacologically important 14-hydroxy-6-oxomorphinans is described. 4,5-Desoxynaltrexone and 4,5-desoxynaloxone were prepared using this route and their biological activities against the opioid receptors were measured.

This article is part of the themed collections: ChemComm 60th Anniversary Collection and Chemical Communications HOT Articles 2024

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DOI: https://doi.org/10.1039/D4CC01788A
Article type: Communication
Submitted: 15 Apr 2024
Accepted: 10 May 2024
First published: 10 May 2024
This article is Open Access

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Chem. Commun., 2024,60, 6007-6010

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Enantioselective de novo synthesis of 14-hydroxy-6-oxomorphinans

J. C. Moore, L. Modell, J. R. Glenn, K. D. Jones, S. P. Argent, J. R. Lane, M. Canals and H. W. Lam, Chem. Commun., 2024, 60, 6007 DOI: 10.1039/D4CC01788A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Chemical Communications

Enantioselective de novo synthesis of 14-hydroxy-6-oxomorphinans†

Abstract

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Enantioselective de novo synthesis of 14-hydroxy-6-oxomorphinans

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