Total Synthesis of Tiacumicin A. Total Synthesis, Relay Synthesis, and Degradation Studies of Fidaxomicin (Tiacumicin B, Lipiarmycin A3)
| Autor: | Hiromu Hattori, Karl Gademann, Regina Berg, Hideki Miyatake-Ondozabal, Elias Kaufmann |
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| Rok vydání: | 2018 |
| Předmět: |
Glycosylation
010405 organic chemistry Chemistry Organic Chemistry Total synthesis 010402 general chemistry Metathesis 01 natural sciences Combinatorial chemistry 0104 chemical sciences Lipiarmycin A3 chemistry.chemical_compound Suzuki reaction Aldol reaction medicine Degradation (geology) Fidaxomicin medicine.drug |
| Zdroj: | The Journal of organic chemistry. 83(13) |
| ISSN: | 1520-6904 |
| Popis: | The commercial macrolide antibiotic fidaxomicin was synthesized in a highly convergent manner. Salient features of this synthesis include a β-selective noviosylation, a β-selective rhamnosylation, a ring-closing metathesis, a Suzuki coupling, and a vinylogous Mukaiyama aldol reaction. Careful choice of protecting groups and fine-tuning of the glycosylation reactions led to the first total synthesis of fidaxomicin. In addition, a relay synthesis of fidaxomicin was established, which gives access to a conveniently protected intermediate from the natural material for derivatization. The first total synthesis of a related congener, tiacumicin A, is presented. |
| Databáze: | OpenAIRE |
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