Secondary metabolites, such as the antibiotics, are often modified with saccharides. The resultant glycosides form heterogeneous “glycoform” mixtures where molecules have similar glycosidic linkages but the saccharides vary in the length, type of monosaccharide unit, and substituents. Chemical synthesis provides a feasible access to the homogeneous glycosides and congeners, thus facilitates studies on their biological and pharmacological activities. Nevertheless, the glycosidic linkages occurring in the natural glycosides are extremely diverse, and many pose formidable challenge to the glycosylation chemistry. Glycosylation of a highly hindered, poorly nucleophilic, or extremely fragile aglycone with an unusual saccharide donor is often required. This lecture shall discuss the challenge and solution of glycosylation chemistry in the context of total synthesis of complex natural glycosides and beyond.<br/>

Tackling the challenge of glycosylation in the syntheses of complex natural glycosides

2019 Fall National Meeting

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