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.


Published in:
Current Organic Chemistry, 4, 5, 455-480
Year:
2000
ISSN:
1385-2728
Keywords:
Note:
Univ Lausanne, Chim Sect, BCH, CH-1015 Lausanne, Switzerland.
Laboratories:




 Record created 2005-11-09, last modified 2018-03-17


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