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

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

Jonathan C Moore  1   2 , Louis Modell  3 , Jacqueline R Glenn  4   5 , Kieran D Jones  1   2 , Stephen P Argent  2 , J Robert Lane  4   5 , Meritxell Canals  4   5 , Hon Wai Lam  1   2
Affiliations

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

Jonathan C Moore et al. Chem Commun (Camb). .

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.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. (A) Representative morphinan opioids. (B) Previous methods for the semisynthesis of 14-hydroxy-6-oxomorphinans without an E-ring.
Scheme 2
Scheme 2. (A) Key synthetic steps. (B) Forward synthesis of 14-hydroxy-6-oxymorphinans without an E-ring.
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