Bergmann, Andreas and Reiser, Oliver (2014) Enantioselective Synthesis of Xanthatin. CHEMISTRY-A EUROPEAN JOURNAL, 20 (25). pp. 7613-7615. ISSN 0947-6539, 1521-3765
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The enantioselective synthesis of cytostatic and antibiotic xanthatin (1a) is reported. As a key intermediate, a bicyclic compound 2 was identified, which can be readily synthesized from methyl-2-furoic acid in diastereo- and enantiomerically pure form. Compound 2 can be functionalized regio- and stereoselectively at C-6 and C-7, allowing the facile introduction of the functionalities found in xanthatin, as well as the synthesis of derivatives thereof. Moreover, a robust strategy for the introduction of the exo-methylene group at C-3, commonly found in many sesquiterpenes, was developed that makes use of masking the alkene in the alpha,beta-unsaturated carbonyl system by O-pivaoyl, which is stable under acidic and mild basic conditions but eliminated upon treatment with strong bases.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | METHYLENE-GAMMA-BUTYROLACTONES; XANTHIUM-STRUMARIUM; ASYMMETRIC-SYNTHESIS; XANTHANOLIDES; DERIVATIVES; EXTRACTS; LACTONES; LEAVES; allylic oxidation; exo-methylene group; synthetic methods; total synthesis; xanthanolides |
| 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: | 28 Oct 2019 08:27 |
| Last Modified: | 28 Oct 2019 08:27 |
| URI: | https://pred.uni-regensburg.de/id/eprint/10018 |
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