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

Chem Commun (Camb). 2024 Jun 6;60(47):6007-6010. doi: 10.1039/d4cc01788a.

Authors

Jonathan C Moore^{1

2}, Louis Modell³, Jacqueline R Glenn^{4

5}, Kieran D Jones^{1

2}, Stephen P Argent², J Robert Lane^{4

5}, Meritxell Canals^{4

5}, Hon Wai Lam^{1

2}

Affiliations

¹ The GlaxoSmithKline Carbon Neutral Laboratories for Sustainable Chemistry, University of Nottingham, Jubilee Campus, Triumph Road, Nottingham, NG7 2TU, UK. [email protected].
² School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.
³ School of Pharmacy, University of Nottingham Biodiscovery Institute, University of Nottingham, Nottingham, NG7 2RD, UK.
⁴ Division of Physiology, Pharmacology and Neuroscience, School of Life Sciences, Queen's Medical Centre, University of Nottingham, Nottingham, NG7 2UH, UK.
⁵ 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.

MeSH terms

Molecular Structure
Morphinans* / chemical synthesis
Morphinans* / chemistry
Naltrexone / analogs & derivatives
Naltrexone / chemical synthesis
Naltrexone / chemistry
Narcotic Antagonists / chemical synthesis
Receptors, Opioid / metabolism
Stereoisomerism

Substances

Morphinans
Naltrexone
Narcotic Antagonists
Receptors, Opioid