Total Syntheses and Biological Assessment of Macrocyclic Glycolipids

Fürstner, Alois

doi:10.1002/ejoc.200300728

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Total Syntheses and Biological Assessment of Macrocyclic Glycolipids

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Fürstner, Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Fürstner, A. (2004). Total Syntheses and Biological Assessment of Macrocyclic Glycolipids. European Journal of Organic Chemistry, (5), 943-958. doi:10.1002/ejoc.200300728.

Cite as: https://hdl.handle.net/11858/00-001M-0000-000F-9739-D

Abstract

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.