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
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Sprache:eng
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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