A Double Decarboxylation Reaction of an Oxazolidinone and Carboxylic Acid: Its Application to the Synthesis of a New Opioid Lead Compound

Treatment of oxazolidinone carboxylic acid 6 with potassium carbonate gave olefin 7 by a double decarboxylation reaction. The reaction was proposed to proceed via decarboxylation followed by E1cB-like mechanism. 15,16-Nornaltrexone derivative 17 prepared from double decarboxylation product 7 showed...

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Veröffentlicht in:	Journal of organic chemistry 2010-02, Vol.75 (3), p.995-998
Hauptverfasser:	Fujii, Hideaki, Imaide, Satomi, Watanabe, Akio, Yoza, Kenji, Nakajima, Mayumi, Nakao, Kaoru, Mochizuki, Hidenori, Sato, Noriko, Nemoto, Toru, Nagase, Hiroshi
Format:	Artikel
Sprache:	eng
Schlagworte:	Analgesics, Opioid - chemical synthesis Analgesics, Opioid - chemistry Analgesics, Opioid - pharmacology Carboxylic Acids - chemistry Catalysis Chemistry Decarboxylation Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Molecular Structure Organic chemistry Oxazolidinones - chemistry Preparations and properties Receptors, Opioid, mu - chemistry Receptors, Opioid, mu - metabolism Spiro Compounds - chemical synthesis Spiro Compounds - chemistry Spiro Compounds - pharmacology
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Zusammenfassung:	Treatment of oxazolidinone carboxylic acid 6 with potassium carbonate gave olefin 7 by a double decarboxylation reaction. The reaction was proposed to proceed via decarboxylation followed by E1cB-like mechanism. 15,16-Nornaltrexone derivative 17 prepared from double decarboxylation product 7 showed strong affinity for the μ opioid receptor, indicating it to be a new opioid lead compound.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo9025463