A lithium hydroxide promoted simple glycosylation of 4-hydroxyindole-3-acet
onitrile with 2,3,4, 6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide was de
veloped. Utilizing the method, the first and five steps total synthesis of
cappariloside A was achieved from indole-3-carbaldehyde in 41% overall yiel
d.