Synthesis of rare carbohydrates and analogues starting from enantiomerically pure 7-oxabicyclo[2.2.1]heptyl derivatives ("naked sugars")
Recent applications of the "naked sugar" methodology are reviewed. General methods have been developed to transform enantiomerically pure 7-oxabicyclo[2.2.1]heptyl derivatives into rare monosaccharides, carbasugars, into a new doubly-branched imino-dideoxyalditol (iminosugar), into long-chain carbohydrates, C-disaccharides, imino-C-disaccharides and new polyhydroxylated quinolizidines. The methods allow to prepare both enantiomers of a given target with the same ease. Predictable high stereoselectivity of the reactions of the bicyclic chirons adds to the flexibility of the approach that can lead to a large molecular diversity.
Keywords: Aza-c-disaccharides ; alpha-glucosidase-i ; beta-d-xyloside ; electron ; donating substituent ; venous antithrombotic agents ; chondroitin sulfate ; chains ; total asymmetric-synthesis ; efficient total synthesis ; ring-expanded analogs ; diels-alder additions
Univ Lausanne, Chim Sect, BCH, CH-1015 Lausanne, Switzerland.
Record created on 2005-11-09, modified on 2016-08-08