In the diploma thesis, a method for preparation of the unsaturated C15-C20 tiacumicin fragment was developed. Tiacumicin is classified as a macrolidone antibiotic. Although three syntheses of tiacumicin have been recently published, this study has aimed to develop a novel pathway for its preparation utilizing catalytic reactions instead of stoichiometric ones. In the second part, an enantioselective allylation of (E)-3-jod-2-methylpropenal has been developed applying catalysis by a series of N,N'-dioxide catalysts. The asymmetric induction achieved in the allylation was up to 99% ee. This procedure allows relatively simple, straightforward and efficient preparation of wide range of natural products. Keywords tiacumicin, asymmetric synthesis, allylation, catalysis, chiral Lewis bases, organocatalysis
| Identifer | oai:union.ndltd.org:nusl.cz/oai:invenio.nusl.cz:364224 |
| Date | January 2017 |
| Creators | Havlíček, Vojtěch |
| Contributors | Kotora, Martin, Veselý, Jan |
| Source Sets | Czech ETDs |
| Language | Czech |
| Detected Language | English |
| Type | info:eu-repo/semantics/masterThesis |
| Rights | info:eu-repo/semantics/restrictedAccess |
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