A Practical, Component-Based Synthetic Route to Methylthiolincosamine Permitting Facile Northern-Half Diversification of Lincosamide Antibiotics
Matthew J. Mitcheltree, Jack W. Stevenson, Amarnath Pisipati, Andrew G. Myers
Abstract
The development of a flexible, component-based synthetic route to the amino sugar fragment of the lincosamide antibiotics is described. This route hinges on the application and extension of nitroaldol chemistry to forge strategic bonds within complex amino sugar targets and employs a glycal epoxide as a versatile glycosyl donor for the installation of anomeric groups. Through building-block exchange and late-stage functionalization, this route affords access to a host of rationally designed lincosamides otherwise inaccessible by semisynthesis and underpins a platform for the discovery of new lincosamide antibiotics.
Topics & Concepts
ChemistryAnomerLincosamidesTotal synthesisAntibioticsCombinatorial chemistryStereochemistryBiochemistryAntibiotic resistanceCarbohydrate Chemistry and SynthesisChemical Synthesis and AnalysisMicrobial Natural Products and Biosynthesis