Sonnleitner, Carina M. and Park, Saerom and Eckl, Robert and Ertl, Thomas and Reiser, Oliver (2020) Stereoselective Synthesis of Tropanes via a 6 pi-Electrocyclic Ring-Opening/ Huisgen [3+2]-Cycloaddition Cascade of Monocyclopropanated Heterocycles. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 59 (41). pp. 18110-18115. ISSN 1433-7851, 1521-3773
Full text not available from this repository. (Request a copy)Abstract
The synthesis of tropanes via a microwave-assisted, stereoselective 6 pi-electrocyclic ring-opening/ Huisgen [3+2]-cycloaddition cascade of cyclopropanated pyrrole and furan derivatives with electron-deficient dipolarophiles is demonstrated. Starting from furans or pyrroles, 8-aza- and 8-oxabicyclo[3.2.1]octanes are accessible in two steps in dia- and enantioselective pure form, being versatile building blocks for the synthesis of pharmaceutically relevant targets, especially for new cocaine analogues bearing various substituents at the C-6/C-7 positions of the tropane ring system. Moreover, the 2-azabicyclo[2.2.2]octane core (isoquinuclidines), being prominently represented in many natural and pharmaceutical products, is accessible via this approach.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | COCAINE C-1 ANALOGS; ENANTIOSELECTIVE SYNTHESIS; FUNCTIONALIZED TROPANES; CYCLOADDITION REACTIONS; ENANTIOMERICALLY PURE; ASYMMETRIC-SYNTHESIS; BINDING-AFFINITY; OPIOID RECEPTORS; NATURAL-PRODUCTS; DOPAMINE; bicyclo[3; 2; 1]octanes; cocaine analogues; furans and pyrroles; isoquinuclidines; microwave-assisted [3+2]-cycloaddition; tropanes |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 16 Mar 2021 07:29 |
| Last Modified: | 16 Mar 2021 07:29 |
| URI: | https://pred.uni-regensburg.de/id/eprint/44005 |
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