Babl, Tobias and Reiser, Oliver (2022) Asymmetric Total Synthesis of Meptazinol. JOURNAL OF ORGANIC CHEMISTRY, 87 (9). pp. 6410-6417. ISSN 0022-3263, 1520-6904
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Thefirst enantioselective synthesis of (S)-meptazi-nol in 14 steps from commercially available ethyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate, being widely used in racemicform for pain treatment, and, en route, the formal synthesis of twoanti-Alzheimer's agents are reported. A novel ring expansion of 2-azabicyclo[4.1.0]heptanes, readily available via the stereoselectivecyclopropanation of 1,2,3,4-tetrahydropyridine-4-ols, provides aneffective entry to 3,3-disubstituted azepanes that represent the core for a variety of approved drugs.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | INHIBITORS; PIPERIDINES; REDUCTION; CHEMISTRY; POTENCY; ENONES; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 07 Nov 2023 14:07 |
| Last Modified: | 07 Nov 2023 14:07 |
| URI: | https://pred.uni-regensburg.de/id/eprint/56706 |
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