Search results for "Morphinan"
showing 10 items of 12 documents
Chromatographically separable rotamers of an unhindered amide
2014
Surprisingly stable formamide rotamers were encountered in the tetrahydroisoquinoline and morphinan series of alkaloids. We investigated the hindered rotation around the amide bond by dynamic high-performance liquid chromatography (DHPLC) and kinetic measurements of the interconversion of the rotamers which can readily be separated by HPLC as well as TLC. The experimental results of the different methods were compared to each other as well as to results obtained by DFT calculations.
On the spectral intermediate at 440 nm formed during mixed function substrate oxidation.
1974
Abstract The spectral shoulder formed at 440 nm in microsomes oxidising hexobarbital and other drugs has been investigated and some of its properties characterised. Hexobarbital, pentobarbital, ethylmorphine and barbital produce this shoulder, while acetanilide, aniline, desmethylimipramine, imipramine, metyrapone and SKF 525-A do not. The formation of the 440 nm shoulder depends on the presence of NADPH and oxygen and is reduced in size when NADH is also present. At saturating substrate concentrations the size of the 440 nm shoulder is correlated to the cytochrome P-450 content. The hexobarbital induced shoulder can be inhibited by drug metabolism inhibitors such as metyrapone, imipramine …
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.
Synthesis of Morphinans through Anodic Aryl‐Aryl Coupling
2021
The morphinans are an important class of structurally fascinating and physiologically important natural products as exemplified by the famous opium alkaloids of the morphine family. Although this class of secondary metabolites from the juice of the opium poppy capsule was already used for medicinal purposes thousands of years ago, chemical modifications are still being applied to the core structure today in order to achieve the most specific effect on the various receptor subtypes possible with the fewest possible side effects. The unusual architecture of the morphinan core has also proven to be a highly challenging target for total synthesis. This review highlights electrosynthetic approac…
CCDC 1894341: Experimental Crystal Structure Determination
2019
Related Article: Alexander Lipp, Maximilian Selt, Dorota Ferenc, Dieter Schollmeyer, Siegfried R. Waldvogel, Till Opatz|2019|Org.Lett.|21|1828|doi:10.1021/acs.orglett.9b00419
CCDC 1831235: Experimental Crystal Structure Determination
2018
Related Article: Alexander Lipp, Dorota Ferenc, Christoph Gütz, Mario Geffe, Nina Vierengel, Dieter Schollmeyer, Hans J. Schäfer, Siegfried R. Waldvogel, Till Opatz|2018|Angew.Chem.,Int.Ed.|57|11055|doi:10.1002/anie.201803887
CCDC 1831232: Experimental Crystal Structure Determination
2018
Related Article: Alexander Lipp, Dorota Ferenc, Christoph Gütz, Mario Geffe, Nina Vierengel, Dieter Schollmeyer, Hans J. Schäfer, Siegfried R. Waldvogel, Till Opatz|2018|Angew.Chem.,Int.Ed.|57|11055|doi:10.1002/anie.201803887
CCDC 1894339: Experimental Crystal Structure Determination
2019
Related Article: Alexander Lipp, Maximilian Selt, Dorota Ferenc, Dieter Schollmeyer, Siegfried R. Waldvogel, Till Opatz|2019|Org.Lett.|21|1828|doi:10.1021/acs.orglett.9b00419
CCDC 1831233: Experimental Crystal Structure Determination
2018
Related Article: Alexander Lipp, Dorota Ferenc, Christoph Gütz, Mario Geffe, Nina Vierengel, Dieter Schollmeyer, Hans J. Schäfer, Siegfried R. Waldvogel, Till Opatz|2018|Angew.Chem.,Int.Ed.|57|11055|doi:10.1002/anie.201803887
CCDC 1831236: Experimental Crystal Structure Determination
2018
Related Article: Alexander Lipp, Dorota Ferenc, Christoph Gütz, Mario Geffe, Nina Vierengel, Dieter Schollmeyer, Hans J. Schäfer, Siegfried R. Waldvogel, Till Opatz|2018|Angew.Chem.,Int.Ed.|57|11055|doi:10.1002/anie.201803887