947231-45-0Relevant articles and documents
Total synthesis of the protected aglycon of fidaxomicin (tiacumicin B, lipiarmycin A3)
Miyatake-Ondozabal, Hideki,Kaufmann, Elias,Gademann, Karl
, p. 1933 - 1936 (2015)
Fidaxomicin, also known as tiacumicin B or lipiarmycin A3, is a novel macrocyclic antibiotic that is used in hospitals for the treatment of Clostridium difficile infections. This natural product has also been shown to have excellent bactericidal activity
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
Synthesis and biological activity of enantiomeric pairs of 5-(alk-2-enyl)thiolactomycin and 5-[(E)-cycloalk-2-enylidenemethyl] thiolactomycin congeners
Ohata, Kohei,Terashima, Shiro
experimental part, p. 920 - 936 (2010/03/23)
The title compounds were synthesized by the efficient route previously explored for the synthesis of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative. These studies were carried out to prove the flexibility of the previously explored synthetic route to natural thiolactomycin (TLM) 1 and to examine the structure-activity relationship on the 5-position of 1. While all of the synthesized congeners lacked in vitro antibacterial activity, these studies led us to find 5-(alk-2-enyl)-TLM (ent-4d) which exhibits mammalian type I fatty acid synthase (FAS) inhibitory activity equal to that of C75, a potent inhibitor reported previously. It was also found that 5-[(E)-cycloalk-2- enylidenemethyl]-TLM (ent-5c) exhibited slightly less potent mammalian type I FAS inhibitory activity than C75.
Synthesis and biological activity of enantiomeric pairs of 5-vinylthiolactomycin congeners
Ohata, Kohei,Terashima, Shiro
, p. 4070 - 4074 (2008/02/07)
Twelve enantiomeric pairs of 5-vinylthiolactomycin congeners were synthesized by employing our efficient synthetic route previously explored for the synthesis of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative. From the biological activ