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 strong affinity for the mu opioid receptor, indicating it to be a new opioid lead compound.
Fujii
Hideaki
H
School of Pharmacy, Kitasato University, 5-9-1, Shirokane, Minato-ku, Tokyo 108-8641, Japan.
Imaide
Satomi
S
Watanabe
Akio
A
Yoza
Kenji
K
Nakajima
Mayumi
M
Nakao
Kaoru
K
Mochizuki
Hidenori
H
Sato
Noriko
N
Nemoto
Toru
T
Nagase
Hiroshi
H
D000701:Analgesics, Opioid / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D003653:Decarboxylation; D015394:Molecular Structure; D023303:Oxazolidinones / Q000737:chemistry*; D017450:Receptors, Opioid, mu / Q000737:chemistry* / Q000378:metabolism*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D000701:Analgesics, Opioid; D002264:Carboxylic Acids; D023303:Oxazolidinones; D017450:Receptors, Opioid, mu; D013141:Spiro Compounds