jo201319b_si_002.cif (53.86 kB)
Total Synthesis of (−)-4,8,10-Tridesmethyl Telithromycin
dataset
posted on 2011-09-16, 00:00 authored by Venkata Velvadapu, Tapas Paul, Bharat Wagh, Ian Glassford, Charles DeBrosse, Rodrigo B. AndradeNovel sources of antibiotics are required to address the serious problem of antibiotic resistance. Telithromycin (2) is a third-generation macrolide antibiotic prepared from erythromycin (1) and used clinically since 2004. Herein we report the details of our efforts that ultimately led to the total synthesis of (−)-4,8,10-tridesmethyl telithromycin (3) wherein methyl groups have been replaced with hydrogens. The synthesis of desmethyl macrolides has emerged as a novel strategy for preparing bioactive antibiotics.