Search results for "Thebaine"
showing 6 items of 6 documents
Enantioselective Synthesis of (−)-Dihydrocodeine and Formal Synthesis of (−)-Thebaine, (−)-Codeine, and (−)-Morphine from a Deprotonated α-Aminonitri…
2014
The α-benzylation of a deprotonated bicyclic α-aminonitrile, followed by Noyori's asymmetric transfer hydrogenation combined with the Grewe cyclization onto a symmetrical A-ring precursor, are the key steps of a short and high-yielding enantioselective synthesis of the morphinan (-)-dihydrocodeine. This compound can be converted to (-)-thebaine in high yield by known transformations, while (-)-codeine and (-)-morphine are available from an advanced intermediate.
ChemInform Abstract: New Studies and a Reinvestigation on (4 + 2) Cycloadditions of (-)- Thebaine: Asymmetrical Diels-Alder Reactions with a Conforma…
2010
Some novel Diels-Alder reactions of the opium alkaloid (−)-thebaine (1) as an electron-rich diene and a reinvestigation of its reactions with cyclic and acyclic dienophiles are described. The π-facial selectivity has been studied on the basis of structural analyses of the cycloadducts. Some related results on [4 + 2] cycloaddition reactions of 1-methoxy-1,3-cyclohexadiene (11) are also reported.
Die direkte quantitative Auswertung von Dünnschichtchromatogrammen durch Remissions- und Fluoreszenzmessungen 3. Mitt.: Bestimmung von Morphin, Codei…
1971
Es wird ein Verfahren zur quantitativen Bestimmung verschiedener Opiumalkaloide nebeneinander beschrieben, das auf der direkten Auswertung von DC durch Remissionsmessung mit Hilfe eines Chromatogramm-Spektralphotometers beruht. Anstelle des bisher ublichen Messpaltes wurde fur die Auswertung eine Kreisblende benutzt. Hierbei ist vorteilhaft, das die Form der Absorptions-Orts-Kurven keinen Einflus auf die Mesgenauigkeit besitzt, da nur die Peakhohe ausgewertet wird. Quantitative Determination of Opium Alkaloids A method for the quantitative determination of a number of single alkaloids in opium alkaloid mixtures is described, which is based on the direct evaluation of TLC by reflectance with…
Back Cover: A Regio- and Diastereoselective Anodic Aryl-Aryl Coupling in the Biomimetic Total Synthesis of (−)-Thebaine (Angew. Chem. Int. Ed. 34/201…
2018
A Regio- and Diastereoselective Anodic Aryl-Aryl Coupling in the Biomimetic Total Synthesis of (-)-Thebaine.
2018
The biosynthesis of thebaine is based on the regioselective, intramolecular, oxidative coupling of (R)-reticuline. For decades, chemists have sought to mimic this coupling by using stoichiometric oxidants. However, all approaches to date have suffered from low yields or the formation of undesired regioisomers. Electrochemistry would represent a sustainable alternative in this respect but all attempts to accomplish an electrochemical synthesis of thebaine have failed so far. Herein, a regio- and diastereoselective anodic coupling of 3',4',5'-trioxygenated laudanosine derivatives is presented, which finally enables electrochemical access to (-)-thebaine.
New Studies and a Reinvestigation on [4+2] Cycloadditions of (−)-Thebaine: Asymmetrical Diels-Alder Reactions with a Conformationally Fixed Chiral Di…
1993
Some novel Diels-Alder reactions of the opium alkaloid (−)-thebaine (1) as an electron-rich diene and a reinvestigation of its reactions with cyclic and acyclic dienophiles are described. The π-facial selectivity has been studied on the basis of structural analyses of the cycloadducts. Some related results on [4 + 2] cycloaddition reactions of 1-methoxy-1,3-cyclohexadiene (11) are also reported.