Kempter, Irina ; Frensch, Britta ; Kopf, Thomas ; Kluge, Ralph ; Csuk, René ; Svoboda, Ingrid ; Fuess, Hartmut ; Hartung, Jens (2014)
Synthesis and structural characterization of the isomuscarines.
In: Tetrahedron, 70 (10)
doi: 10.1016/j.tet.2013.12.085
Artikel, Bibliographie
Kurzbeschreibung (Abstract)
Four diastereomers of 2-[(trimethylammonium)-methyl]-5-methyltetrahydrofuran-3-ol, trivially named isomuscarine, allo-isomuscarine, epi-isomuscarine, and epiallo-isomuscarine, were prepared as bromide salts from 2,4-like and 2,4-unlike diastereomers of 3-(4-hydroxyhex-5-en-2-oxy)-4-methylthiazole-2(3H)-thione. The strategy for constructing the tetrahydrofuran nucleus of the isomuscarines uses alkenoxyl radical 5-exo-bromocyclization, occurring 2,3-cis-selectively for the 2,4-like-4-hydroxyhex-5-en-2-oxyl radical, and 2,3-trans-selectively for the 2,4-unlike diastereomer. A fraction of 4-hydroxyhex-5-en-2-oxyl radicals cyclizes 6-endo-selectively providing 5-bromo-2-methyltetrahydropyran-4-ols in yields between 3 and 15%. Substituting trimethylamine for bromide in 5-exo-bromocyclized products furnishes isomuscarine bromides, which were structurally characterized by X-ray diffraction and NMR-spectroscopy.
| Typ des Eintrags: | Artikel |
|---|---|
| Erschienen: | 2014 |
| Autor(en): | Kempter, Irina ; Frensch, Britta ; Kopf, Thomas ; Kluge, Ralph ; Csuk, René ; Svoboda, Ingrid ; Fuess, Hartmut ; Hartung, Jens |
| Art des Eintrags: | Bibliographie |
| Titel: | Synthesis and structural characterization of the isomuscarines |
| Sprache: | Englisch |
| Publikationsjahr: | 11 März 2014 |
| Verlag: | Elsevier Science Publishing |
| Titel der Zeitschrift, Zeitung oder Schriftenreihe: | Tetrahedron |
| Jahrgang/Volume einer Zeitschrift: | 70 |
| (Heft-)Nummer: | 10 |
| DOI: | 10.1016/j.tet.2013.12.085 |
| Kurzbeschreibung (Abstract): | Four diastereomers of 2-[(trimethylammonium)-methyl]-5-methyltetrahydrofuran-3-ol, trivially named isomuscarine, allo-isomuscarine, epi-isomuscarine, and epiallo-isomuscarine, were prepared as bromide salts from 2,4-like and 2,4-unlike diastereomers of 3-(4-hydroxyhex-5-en-2-oxy)-4-methylthiazole-2(3H)-thione. The strategy for constructing the tetrahydrofuran nucleus of the isomuscarines uses alkenoxyl radical 5-exo-bromocyclization, occurring 2,3-cis-selectively for the 2,4-like-4-hydroxyhex-5-en-2-oxyl radical, and 2,3-trans-selectively for the 2,4-unlike diastereomer. A fraction of 4-hydroxyhex-5-en-2-oxyl radicals cyclizes 6-endo-selectively providing 5-bromo-2-methyltetrahydropyran-4-ols in yields between 3 and 15%. Substituting trimethylamine for bromide in 5-exo-bromocyclized products furnishes isomuscarine bromides, which were structurally characterized by X-ray diffraction and NMR-spectroscopy. |
| Freie Schlagworte: | Alkoxyl radical, Bromocyclization, Muscarine alkaloid, Stereoselective synthesis, Tetrahydrofuran, Thiazolethione |
| Fachbereich(e)/-gebiet(e): | 11 Fachbereich Material- und Geowissenschaften > Materialwissenschaft > Fachgebiet Strukturforschung 11 Fachbereich Material- und Geowissenschaften > Materialwissenschaft 11 Fachbereich Material- und Geowissenschaften |
| Hinterlegungsdatum: | 23 Jan 2015 09:04 |
| Letzte Änderung: | 23 Jan 2015 09:04 |
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