Carbohydrates and their analogs are key molecules with a wide range of
biological activities. These bioactive compounds are usually synthesized through
derivatization of naturally occurring carbohydrates. Nevertheless, this strategy suffers from a
limited range of naturally available monosaccharide building blocks and the necessity of
laborious steps of protection and deprotection. Consequently new methods began to emerge
and Diels-Alder reaction appeared to be a method of choice for their de novo production.
The synthesis of carbohydrates and their analogs by means of cycloaddition reactions will be
reviewed here. Moreover the potentiality of the use of monosaccharides to induce chirality in
Diels-Alder reaction will be presented. Efficient methods for the synthesis of di- and trisaccharides
using the developments shown previously will be also introduced.
Keywords: Asymmetric synthesis, aza-sugars, carbohydrates, chiral auxiliary, diels-Alder, disaccharides, hetero-Diels-Alder reaction, thiosugars.
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