title: A double decarboxylation reaction of an oxazolidinone and carboxylic Acid: its application to the synthesis of a new opioid lead compound.
abstract: 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.
authors.affiliation: School of Pharmacy, Kitasato University, 5-9-1, Shirokane, Minato-ku, Tokyo 108-8641, Japan.
authors.forename: Hideaki
authors.initials: H
authors.lastname: Fujii
authors.forename: Satomi
authors.initials: S
authors.lastname: Imaide
authors.forename: Akio
authors.initials: A
authors.lastname: Watanabe
authors.forename: Kenji
authors.initials: K
authors.lastname: Yoza
authors.forename: Mayumi
authors.initials: M
authors.lastname: Nakajima
authors.forename: Kaoru
authors.initials: K
authors.lastname: Nakao
authors.forename: Hidenori
authors.initials: H
authors.lastname: Mochizuki
authors.forename: Noriko
authors.initials: N
authors.lastname: Sato
authors.forename: Toru
authors.initials: T
authors.lastname: Nemoto
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Nagase
mesh_terms: 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
chemical_list: D000701:Analgesics, Opioid; D002264:Carboxylic Acids; D023303:Oxazolidinones; D017450:Receptors, Opioid, mu; D013141:Spiro Compounds