Direct Synthesis of Naltrexone by Palladium‐Catalyzed  N ‐Demethylation/Acylation of Oxymorphone: The Benefit of CH Activation and the Intramolecular Acyl Transfer from C‐14 Hydroxy | Zendy

Machara Ales | Zendy; Cox D. Phillip | Zendy; Hudlicky Tomas | Zendy

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Direct Synthesis of Naltrexone by Palladium‐Catalyzed N ‐Demethylation/Acylation of Oxymorphone: The Benefit of CH Activation and the Intramolecular Acyl Transfer from C‐14 Hydroxy

Author(s) -

Machara Ales,

Cox D. Phillip,

Hudlicky Tomas

Publication year - 2012

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201200677

Subject(s) - chemistry , oxymorphone , intramolecular force , acylation , naltrexone , palladium , demethylation , stereochemistry , medicinal chemistry , catalysis , organic chemistry , opioid , biochemistry , oxycodone , receptor , gene expression , dna methylation , gene

Oxymorphone was converted to naltrexone in three steps by palladium‐catalyzed oxidative N ‐demethylation and intramolecular acyl transfer from C‐14 hydroxy to N‐17. Vitride™ reduction of N ‐acylamide to N ‐alkylamine proceeded with concomitant reductive deprotection of C‐6 and O‐3 functionalities.

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