Brunner, Henri and Ittner, Karl-Peter and Lunz, Dirk and Schmatloch, Stefan and Schmidt, Thomas and Zabel, Manfred (2003) Highly enriched mixtures of methohexital stereoisomers by palladium-catalyzed allylation and their anaesthetic activity. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (5). pp. 855-862. ISSN 1434-193X
Full text not available from this repository. (Request a copy)Abstract
The stereoselective Pd-catalyzed allylation of MBA [5-(2'hex-3'-ynyl)-1-methylbarbituric acid] gives the commercial injection narcotic methohexital, which exists as four isomers: two diastereomeric pairs of enantiomers. The isomer composition produced depends on three stereochemical parameters: catalyst control, substrate control, and kinetic resolution. Judicious choice of these parameters allowed the synthesis of methohexital samples with greatly differing isomer compositions, and these samples were investigated with re-spect to their anaesthetic doses in rats. Some isomer compositions obtained were much more active than the commercially used drug and showed fewer side effects. As a consequence of the determination of the absolute configuration of the methohexital (SbRh) isomer, the unknown configuration of the trade product, the so-called a-racemate, can be established as (RbSh) and (SbRh). (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ASYMMETRIC CATALYSIS; allylation; catalysis; kinetic resolution; palladium; stereoselectivity |
| Subjects: | 500 Science > 540 Chemistry & allied sciences 600 Technology > 610 Medical sciences Medicine |
| Divisions: | Medicine > Lehrstuhl für Anästhesiologie Medicine > Lehreinheit Pharmakologie Chemistry and Pharmacy > Institut für Anorganische Chemie > Alumni or Retired Professors > Prof. Dr. Henri Brunner |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 24 Aug 2021 10:41 |
| Last Modified: | 24 Aug 2021 10:41 |
| URI: | https://pred.uni-regensburg.de/id/eprint/39228 |
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