512
3
Chemical Glycosylation Reactions
⊡ Scheme 43
Dihydroxyphenyl glycosides are a family of plant components. Some representatives have also
been synthesized based on the trichloroacetimidate method, such as for instance the conandroside [288]. Other plant metabolites, such as for instance the ellagitannins, contain benzoyl
groups at the anomeric oxygen. The derived coriariin A (43d, > Scheme 43) was obtained as
discussed above just by heating 43b with glycosyl donor 43a, leading to 43c, which was transformed into target molecule 43d [289]. Macrophylloside D [290] and buprestin A [291] were
similarly prepared.
N-Glycosylation of nitrogen-containing heterocycles has also been investigated. An interesting synthesis of N-indigoglycosides was undertaken which, as analogs of akashines, exhibit
activity against various human tumor cell lines [292].
Unique glycolipids produced by plants are the resin glycosides for which the first synthesis was
based on the trichloroacetimidate method [293,294]. Other members of this family have been
3
Chemical Glycosylation Reactions
⊡ Scheme 43
Dihydroxyphenyl glycosides are a family of plant components. Some representatives have also
been synthesized based on the trichloroacetimidate method, such as for instance the conandroside [288]. Other plant metabolites, such as for instance the ellagitannins, contain benzoyl
groups at the anomeric oxygen. The derived coriariin A (43d, > Scheme 43) was obtained as
discussed above just by heating 43b with glycosyl donor 43a, leading to 43c, which was transformed into target molecule 43d [289]. Macrophylloside D [290] and buprestin A [291] were
similarly prepared.
N-Glycosylation of nitrogen-containing heterocycles has also been investigated. An interesting synthesis of N-indigoglycosides was undertaken which, as analogs of akashines, exhibit
activity against various human tumor cell lines [292].
Unique glycolipids produced by plants are the resin glycosides for which the first synthesis was
based on the trichloroacetimidate method [293,294]. Other members of this family have been