57783-59-2Relevant academic research and scientific papers
Total Synthesis of the Glycosylated Macrolide Antibiotic Fidaxomicin
Kaufmann, Elias,Hattori, Hiromu,Miyatake-Ondozabal, Hideki,Gademann, Karl
, p. 3514 - 3517 (2015)
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
Total Synthesis of Tiacumicin A. Total Synthesis, Relay Synthesis, and Degradation Studies of Fidaxomicin (Tiacumicin B, Lipiarmycin A3)
Hattori, Hiromu,Kaufmann, Elias,Miyatake-Ondozabal, Hideki,Berg, Regina,Gademann, Karl
, p. 7180 - 7205 (2018/07/15)
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 vinylo
The nitrile oxide/isoxazoline approach to eleven-carbon monosaccharides: cycloaddition of D- and L-arabinonitrile oxides to 5,6-dideoxyhex-5-enofuranoses and characterisation of the resulting 2-isoxazolines
Gould, Robert O.,McGhie, Karen E.,Paton, R. Michael
, p. 1 - 13 (2007/10/03)
Cycloaddition of 2,3:4,5-di-O-isopropylidene-D-arabinonitrile oxide 5, generated by base-induced dehydrochlorination of hydroximoyl chloride 10, to D-Glc-derived alkene 7 afforded an 89:11 diastereomeric mixture of (5R)- and (5S)-3-(1,2:3,4-di-O-isopropyl
?-FACIAL SELECTIVITY IN THE CYCLOADDITION OF NITRILE OXIDES TO 5,6-DIDEOXY-5-ENOFURANOSES
Blake, Alexander J.,Kirkpatrick, Graeme,McGhie, Karen E.,Paton, R. Michael,Penman, Kenneth J.
, p. 409 - 420 (2007/10/02)
Benzonitrile oxide and ethoxycarbonylformonitrile oxide cycloadd regiospecifically and diastereoselectively to α-methyl 5,6-dideoxy-2,3-O-isopropylidene-Δ-lyxo-hex-5-enofuranoside 7 to afford isoxazolines 10 and 11.The ?-facial selectivity (ca. 7:1) is co
