Publication: Total synthesis of the glycosylated macrolide antibiotic fidaxomicin
Total synthesis of the glycosylated macrolide antibiotic fidaxomicin
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Kaufmann, E., Hattori, H., Miyatake-Ondozabal, H., & Gademann, K. (2015). Total synthesis of the glycosylated macrolide antibiotic fidaxomicin. Organic Letters, 17(14), 3514–3517. https://doi.org/10.1021/acs.orglett.5b01602
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Abstract
The first enantioselective total synthesis of fidaxomicin, also known as tiacumicin B or lipiarmycin A3, is reported. This novel glycosylated macrolide antibiotic is used in the clinic for the treatment of Clostridium difficile infections. Key features of the synthesis involve a rapid and high-yielding access to the noviose, rhamnose, and orsellinic acid precursors; the first example of a β-selective noviosylation; an effective Suzuki coupling of highly functionalized substrates; and a ring-closing metathesis reaction of a noviosylate
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- Kaufmann, Elias
- Hattori, Hiromu
- Miyatake-Ondozabal, Hideki
- Gademann, Karl
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Kaufmann, E., Hattori, H., Miyatake-Ondozabal, H., & Gademann, K. (2015). Total synthesis of the glycosylated macrolide antibiotic fidaxomicin. Organic Letters, 17(14), 3514–3517. https://doi.org/10.1021/acs.orglett.5b01602
