A Practical, Component-Based Synthetic Route to Methylthiolincosamine Permitting Facile Northern-Half Diversification of Lincosamide Antibiotics

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The development of a flexible, component-based synthetic route to the aminosugar fragment of the lincosamide antibiotics is described. This synthetic route hinges on the application and extension of nitroaldol chemistry to forge strategic bonds within complex aminosugar targets, and employs a glycal epoxide as a versatile glycosyl donor for the installation of various 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.