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Total Syntheses and Biological Assessment of Macrocyclic Glycolipids
Author(s) -
Fürstner Alois
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300728
Subject(s) - chemistry , alkene , glycolipid , ring closing metathesis , alkyne , total synthesis , organic chemistry , amphiphile , lactone , metathesis , stereochemistry , glycoside , ring (chemistry) , combinatorial chemistry , biochemistry , copolymer , catalysis , polymer , polymerization
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 B 1 , glucolipsin A, and various analogues thereof. A brief survey of the biological activities exerted by these amphiphilic natural products is provided. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)