Catalytic site-selective synthesis and evaluation of a series of erythromycin analogs
The generation of a series of analogs of erythromycin A (EryA, 2) is described. In this study, we compared two peptide-based catalysts-one originally identified from a catalyst screen (5) and its enantiomer (ent-5)-for the selective functionalization of EryA. The semi-synthetic analogs were subjected to MIC evaluation with two bacterial strains and compared to unfunctionalized EryA.
Lewis, Chad A.,Merkel, Janie,Miller, Scott J.
supporting information; experimental part
p. 6007 - 6011
(2009/06/25)
Site-selective derivatization and remodeling of erythromycin A by using simple peptide-based chiral catalysts
(Chemical Equation Presented) Reversal: Simple peptide-based nucleophilic catalysts can perturb the inherent reactivity hierarchy of the polyol natural product erythromycin A (see picture). Such catalyst-dependent modifications that reorganize natural product architecture may be of utility for generation of natural product analogs.