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

doi:10.1021/jo9025463

Paper

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

Published Feb 5, 2010 · H. Fujii, Satomi Imaide, A. Watanabe

The Journal of organic chemistry

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13

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0

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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.

Study Snapshot

The double decarboxylation reaction of oxazolidinone and carboxylic acid led to the synthesis of a new opioid lead compound with strong affinity for the mu opioid receptor.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

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

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References

Citations

Unexpected Rearrangement Reactions of the 14-Aminonaltrexone Skeleton.

14-aminonaltrexone reacts with acetic anhydride to produce novel compounds with morphinan-type skeletons, some of which show binding to opioid receptors.

Essential structure of orexin 1 receptor antagonist YNT-707, part V: Structure-activity relationship study of the substituents on the 17-amino group.

The 17-N-Boc derivative 14a shows the most potent orexin 1 receptor antagonistic activity, with increased bulkiness of 17-substituents leading to increased antagonistic activity.

Essential structure of orexin 1 receptor antagonist YNT-707, Part IV: The role of D-ring in 4,5-epoxymorphinan on the orexin 1 receptor antagonistic activity.

The D-ring in 4,5-epoxymorphinan plays a crucial role in the orexin 1 receptor antagonistic activity of YNT-707, providing a useful scaffold for further design of orexin 1 receptor ligands.

Asymmetric Total Syntheses of Insulicolide A, 14- O-Acetylinsulicolide A, 6β,9α-Dihydroxy-14- p-nitrobenzoylcinnamolide, and 7α,14-Dihydroxy-6β- p-nitrobenzoylconfertifolin.

This study demonstrates the first-ever asymmetric total syntheses of insulicolide A, 14-O-acetylinsulicolide A, 6,9-dihydroxy-14-p-nitrobenzoylcinnamolide, and 7,14-di

Synthesis of Chiral Dihydrobenzofurans and Phthalides by Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution: A Strategy for Total Synthesis of Daldinins A, B, and C and Concentricolide

This study presents a versatile strategy for the total synthesis of anti-HIV-1 agent concentricolide and its analogues daldinins A, B, and C, offering a mild and facile access to these benzo annulated compounds with multiple stereocenters in good yield.