Kreuzer, Andreas and Kerres, Sabine and Ertl, Thomas and Ruecker, Hannelore and Amslinger, Sabine and Reiser, Oliver (2013) Asymmetric Synthesis of Both Enantiomers of Arteludovicinolide A. ORGANIC LETTERS, 15 (13). pp. 3420-3423. ISSN 1523-7060,
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The first total synthesis of either enantiomer of Arteludovicinolide A and their biological evaluation is reported, featuring a new strategy for the asymmetric construction of gamma-butyrolactones with stereogenic side chains in the 4-position. Starting from the renewable resource methyl 2-furoate, the sesquiterpene lactone was synthesized in 9 steps and 4.8% overall yield via an asymmetric cyclopropanation and two diastereoselective nucleophile additions making use of a donor-acceptor-cyclopropane-lactonization cascade. At noncytotoxic concentrations (<= 10 mu M) (+)-1 was found to have a 15 times higher anti-inflammatory activity (4.87 +/- 1.1 mu M) than previously reported for concentrations of >= 45 mu M.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | SESQUITERPENE LACTONES; ENANTIOSELECTIVE SYNTHESIS; PARACONIC ACIDS; GUAIANOLIDES; CONSTITUENTS; PRECURSORS; OLEFINS; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Dr. Sabine Amslinger |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 06 Apr 2020 09:38 |
| Last Modified: | 06 Apr 2020 09:38 |
| URI: | https://pred.uni-regensburg.de/id/eprint/16376 |
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