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Schlagwörter:
carbohydrates; glycosides; macrolides; metathesis; natural products
Zusammenfassung:
Novel strategies for the synthesis of structurally complex macrocyclic glycolipids are outlined which have opened concise and highly flexible entries into various resin glycosides and sugar-based macrodiolides. The key design elements consist of either a ring-closing alkene (RCM) or alkyne metathesis (RCAM) event or a newly developed template-directed dilactonization reaction. The performance and excellent application profile of these transformations are illustrated by the total syntheses of tricolorin A and G, woodrosin I, sophorolipid lactone, cycloviracin B1, glucolipsin A, and various analogues thereof. A brief survey of the biological activities exerted by these amphiphilic natural products is provided.
