A double decarboxylation reaction of an oxazolidinone and carboxylic Acid: its application to the synthesis of a new opioid lead compound

Hideaki Fujii; Satomi Imaide; Akio Watanabe; Kenji Yoza; Mayumi Nakajima; Kaoru Nakao; Hidenori Mochizuki; Noriko Sato; Toru Nemoto; Hiroshi Nagase

doi:10.1021/jo9025463

A double decarboxylation reaction of an oxazolidinone and carboxylic Acid: its application to the synthesis of a new opioid lead compound

J Org Chem. 2010 Feb 5;75(3):995-8. doi: 10.1021/jo9025463.

Authors

Hideaki Fujii¹, Satomi Imaide, Akio Watanabe, Kenji Yoza, Mayumi Nakajima, Kaoru Nakao, Hidenori Mochizuki, Noriko Sato, Toru Nemoto, Hiroshi Nagase

Affiliation

¹ School of Pharmacy, Kitasato University, 5-9-1, Shirokane, Minato-ku, Tokyo 108-8641, Japan.

PMID: 20070096
DOI: 10.1021/jo9025463

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Analgesics, Opioid / chemical synthesis*
Analgesics, Opioid / chemistry
Analgesics, Opioid / pharmacology
Carboxylic Acids / chemistry*
Catalysis
Decarboxylation
Molecular Structure
Oxazolidinones / chemistry*
Receptors, Opioid, mu / chemistry*
Receptors, Opioid, mu / metabolism*
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry
Spiro Compounds / pharmacology

Substances

Analgesics, Opioid
Carboxylic Acids
Oxazolidinones
Receptors, Opioid, mu
Spiro Compounds